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Potassium Carbonate → Methyl 4-((2s)-2-{[(tert-butoxycarbonyl)((2s)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-phenoxypropyl)amino]methyl}-3,4-dihydro-2h-chromen-6-yl)-2-hydroxybenzoate

HRID 47694
Notes
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Reaction equation

HRID 47694 reaction equation
[Si:1]([O:8][C@H:9]([CH2:43][O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:10][N:11]([CH2:19][C@@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:30]3[CH:31]=[CH:32][C:33]4[C:38](=[O:39])[O:37][C:36](C)(C)[O:35][C:34]=4[CH:42]=3)[CH:26]=2)[O:21]1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:14]([O:13][C:12]([N:11]([CH2:19][C@@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:30]3[CH:31]=[CH:32][C:33]([C:38]([O:37][CH3:36])=[O:39])=[C:34]([OH:35])[CH:42]=3)[CH:26]=2)[O:21]1)[CH2:10][C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])[CH2:43][O:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:18])([CH3:15])([CH3:16])[CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86587740tert-butyl (2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-phenoxypropyl{[(2S)-6-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)-3,4-dihydro-2H-chromen-2-yl]methyl}carbamate

Product 1

HCID 69895945Methyl 4-((2s)-2-{[(tert-butoxycarbonyl)((2s)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-phenoxypropyl)amino]methyl}-3,4-dihydro-2h-chromen-6-yl)-2-hydroxybenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To a solution of Example 204 (0.8 g, 1.14 mmol, 1.0 eq.) in methanol (10 mL) was added potassium carbonate (0.078 g, 0.57 mmol, 0.5 eq.) at room temperature. The reaction mixture was allowed to stir at room temperature for 18 hours and then concentrated under reduced pressure. The resulting residue was washed with distilled water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the desired product as pale yellow oil (0.75 g, 97%). 1H NMR (CDCl3) δ10.68 (s, 1 H), 7.73 (d, 1H), 7.26-7.14 (m, 4H), 6.94 (dd, 1H), 6.86-6.75 (m, 5H), 4.21-4.02 (m, 2H), 3.83 (s, 3H), 3.80-3.56 (m, 4H), 3.40-3.21 (m, 2H), 2.80-2.67 (m, 2H), 1.95-1.92 (m, 1H), 1.65-1.60 (m, 1H), 1.38 (s, 9H), 0.83 (s, 9H), 0.001 (s, 6H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe resulting residue was washed with distilled water (10 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-479d7073bf434ca5af8b75d104644ba6
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699860B2

Reaction notes

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