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Chloromethyl Methyl Ether → Glycine tert-butyl ester hydrochloride

HRID 1364361
Notes
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Reaction equation

HRID 1364361 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH3:39])=[C:6]([CH:37]=1)[CH2:7][CH:8]1[C:14](=[O:15])[N:13]([C:16]([NH:18][C@H:19]([CH2:34][CH3:35])[C:20]([NH:22][C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=2[O:32]C)[C:26]([OH:28])=[O:27])=[O:21])=[O:17])[CH2:12][C:11](=[O:36])[NH:10][CH2:9]1.OC1C=C[C:44]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=CC=1[N+]([O-])=O.ClCOC.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.C(Cl)Cl>[ClH:1].[C:48]([O:47][C:45](=[O:46])[CH2:44][NH2:10])([CH3:51])([CH3:50])[CH3:49].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH3:39])=[C:6]([CH:37]=1)[CH2:7][CH:8]1[C:14](=[O:15])[N:13]([C:16]([NH:18][C@H:19]([CH2:34][CH3:35])[C:20]([NH:22][C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=2[OH:32])[C:26]([OH:28])=[O:27])=[O:21])=[O:17])[CH2:12][C:11](=[O:36])[NH:10][CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 22667857Tert-butyl 4-hydroxy-3-nitrobenzoateHCID 576710433-{[(2r)-2-({[6-(5-Chloro-2-methoxybenzyl)-3,7-dioxo-1,4-diazepan-1-yl]carbonyl}amino)butanoyl]amino}-4-methoxybenzoic acid

Product 2

HCID 2725036Glycine tert-butyl ester hydrochloride
HCID 57671109
3-{[(2R)-2-({[6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-1,4-diazepan-1-yl]carbonyl}amino)butanoyl]amino-}-4-hydroxybenzoic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the synthesis intermediate of Example 265, that is, tert-butyl 4-hydroxy-3-nitrobenzoate (0.42 g), methylene chloride (10 ml), chloromethylmethylether (0.16 ml), and N,N-diisopropylethylamine (0.37 ml) were added under ice cooling and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate and successively washed with water, a potassium hydrogensulfate aqueous solution, and saturated saline. The mixture was dried over with anhydrous magnesium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1). To the obtained tert-butyl 4-methoxymethyloxy-3-nitrobenzoate (0.26 g), ethanol (10 ml) and 10% palladium carbon (40 mg) were added and the mixture was stirred under hydrogen atmosphere at room temperature for 7 hours. The reaction solution was filtered, the filtrate was concentrated, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 1/1). The obtained tert-butyl 3-amino-2-methoxymethyloxybenzoate was used, instead of the starting material compound of Example 220, that is, the glycine tert-butyl ester hydrochloride, for the similar procedure as in Example 220 and Example 245 to obtain the title compound.

Workup

  1. washsuccessively washed with water
  2. dry with materialThe mixture was dried over with anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)
  5. additionTo the obtained tert-butyl 4-methoxymethyloxy-3-nitrobenzoate (0.26 g), ethanol (10 ml) and 10% palladium carbon (40 mg) were added
  6. stirringthe mixture was stirred under hydrogen atmosphere at room temperature for 7 hours
  7. filtrationThe reaction solution was filtered
  8. concentrationthe filtrate was concentrated
  9. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 1/1)

Sources & evidence

ORD record
ord-22ea0ad1a54045c1b7e9a1e878e70d93
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07888348B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes