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Diisopropylethylamine → tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate

HRID 2389334
Notes
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Reaction equation

HRID 2389334 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:8][OH:9])[C:4]([O:6][CH3:7])=[O:5].[C:10]([O:14][C:15]([N:17]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:26](O)=[O:27])[C:20]=2[CH:19]=[CH:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)C(C)C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C.O>[OH:9][CH2:8][C@H:3]([NH:2][C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[CH:19]=[CH:18][N:17]2[C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])=[O:27])[C:4]([O:6][CH3:7])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 497588501-Boc-4-carboxyindole

Product 1

HCID 68536502tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylateYield 72.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (1.25 g), 1-(tert-butoxycarbonyl)-1H-indole-4-carboxylic acid (2.10 g) and N-ethyl-N-isopropyl-2-propanamine (2.94 mL) in DMF (25.0 mL) was added dropwise DPPA (1.91 mL) at 0° C. and the mixture was stirred at ambient temperature for 3 days. The resulting mixture was diluted with water (50.0 mL) and extracted with EtOAc (75 mL). The organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution. and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=99:1) to afford tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate (2.12 g) as a colorless syrup.

Workup

  1. extractionextracted with EtOAc (75 mL)
  2. washThe organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution
  3. dry with materialand brine, dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=99:1)

Sources & evidence

ORD record
ord-34eb15dc93cc451596386ad354cc21ed
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273745B2

Reaction notes

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