Methanol → HCID 69215566, compound

HRID 1280970Notes

Reaction equation

HRID 1280970 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:35])[CH2:13][NH:14][C:15](=[O:34])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:7]1.[C:41](OC(=O)C)(=[O:43])[CH3:42].CO>N1C=CC=CC=1>[C:41]([NH:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:35])[CH2:13][NH:14][C:15](=[O:34])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:7]1)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 54451378HCID 54451378, compound

Product 1

HCID 69215566HCID 69215566, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (R)-1-(3-amino-4-methoxybenzyl)-3-[{N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine (50.5 mg) in pyridine (1 mL) was added acetic anhydride (1 mL). The reaction mixture was stirred at room temperature overnight and methanol was added. The mixture was evaporated, and 1 N NaOH solution was added. The mixture was extracted with ethyl acetate and the organic layer was concentrated. Preparative TLC gave (R)-1-(3-acetylamino-4-methoxybenzyl)-3-[{N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine.

Workup

  1. customThe mixture was evaporated
  2. addition1 N NaOH solution was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-8fc9ff641b6b4e67bfdc83371530f537
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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