Methanol → HCID 24949336, compound

HRID 2357350Notes

Reaction equation

HRID 2357350 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:19]=[N:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[NH:31][C:32]([C@@H:35]5[CH2:39][CH2:38][CH2:37][N:36]5[C:40](=[O:53])[C@H:41]([NH:48][C:49]([O:51][CH3:52])=[O:50])[C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)=[N:33][CH:34]=4)=[CH:26][CH:25]=3)=[N:22][CH:23]=2)=[CH:16][N:17]=1)=O)(C)(C)C.CO>CCOCC>[CH3:52][O:51][C:49](=[O:50])[NH:48][C@H:41]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:40](=[O:53])[N:36]1[CH2:37][CH2:38][CH2:39][C@H:35]1[C:32]1[NH:31][C:30]([C:27]2[CH:28]=[CH:29][C:24]([C:21]3[N:22]=[CH:23][C:18]([C:15]4[NH:14][C:13]([C@@H:9]5[CH2:10][CH2:11][CH2:12][NH:8]5)=[N:17][CH:16]=4)=[CH:19][N:20]=3)=[CH:25][CH:26]=2)=[CH:34][N:33]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 24951126(S)-2-{5-[2-(4-{2-[(S)-1-((R)-2-methoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-pyrimidin-5-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 24949336HCID 24949336, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cold (0° C.) 4 NHCl in dioxanes (4 mL) was added via syringe to (S)-2-{5-[2-(4-{2-[(S)-1-((R)-2-methoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-pyrimidin-5-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (104.6 mg, 0.146 mmol) in a 100 mL pear-shaped flask followed by MeOH (0.5 mL). The homogeneous mixture was stirred at room temperature for 15 min before a precipitate was observed. After stirring further for 1.75 h, the suspension was diluted with ether and hexanes. Suction-filtration of a small portion of the suspension yielded the title compound as a yellow solid which was used for characterization purposes. The balance of the suspension was concentrated down to dryness and placed under high vacuum for 16 h. There was isolated the rest of the title compound also as a yellow solid (137.7 mg, 123%) which was used without further purification.

Workup

  1. stirringAfter stirring further for 1.75 h
  2. filtrationSuction-filtration of a small portion of the suspension

Sources & evidence

ORD record
ord-9a8fefec60a84ecda48e2ae21c4f8a08
Source dataset
uspto-grants-2010_07
Patent number
US07759495B2

Reaction notes

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