Methanol → HCID 69215566, compound

HRID 279273Notes

Reaction equation

HRID 279273 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-86aff3186fd34875b33dc508299335fd
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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