Citric Acid → HCID 19050064, compound

HRID 1780219Notes

Reaction equation

HRID 1780219 reaction equation
C([O:4][CH2:5][CH:6]1[C:10]2=[C:11]3[C:15](=[C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:17]=[C:9]2[N:8]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:7]1)[NH:14][C:13]([C:26]([F:29])([F:28])[F:27])=[C:12]3[C:30]([O:32][CH3:33])=[O:31])(=O)C.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[CH2:19]([O:18][C:16]1[CH:17]=[C:9]2[N:8]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:7][CH:6]([CH2:5][OH:4])[C:10]2=[C:11]2[C:15]=1[NH:14][C:13]([C:26]([F:27])([F:28])[F:29])=[C:12]2[C:30]([O:32][CH3:33])=[O:31])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 19050092HCID 19050092, compound

Product 1

HCID 19050064HCID 19050064, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 4 ml of methanol, was suspended 225 mg (0.4 mmol) of methyl 1-acetoxymethyl-5-benzyloxy-3-t-butoxycarbonyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate. Thereto 110.6 mg (0.8 mmol) of potassium carbonate was added, and the mixture was stirred for 7 hours. It was neutralized with 10% citric acid, and diluted with water. The precipitated crystalline matter was collected by filtration, washed with water, and dried. Thereby, methyl 5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate was prepared in a colorless crystalline state in a yield of 206.5 mg (99%).

Workup

  1. filtrationThe precipitated crystalline matter was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-149b74907e514a31a17f6dc8e5d747ae
Source dataset
uspto-grants-1997_05
Patent number
US05629430

Reaction notes

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