Hydrochloric Acid → HCID 24949336, compound

HRID 1484266Notes

Reaction equation

HRID 1484266 reaction equation
Cl.C(OC([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:15][C:16]([C:19]2[CH:20]=[N:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[NH:32][C:33]([C@@H:36]5[CH2:40][CH2:39][CH2:38][N:37]5[C:41](=[O:54])[C@H:42]([NH:49][C:50]([O:52][CH3:53])=[O:51])[C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)=[N:34][CH:35]=4)=[CH:27][CH:26]=3)=[N:23][CH:24]=2)=[CH:17][N:18]=1)=O)(C)(C)C.CO>CCOCC>[CH3:53][O:52][C:50](=[O:51])[NH:49][C@H:42]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:41](=[O:54])[N:37]1[CH2:38][CH2:39][CH2:40][C@H:36]1[C:33]1[NH:32][C:31]([C:28]2[CH:29]=[CH:30][C:25]([C:22]3[N:23]=[CH:24][C:19]([C:16]4[NH:15][C:14]([C@@H:10]5[CH2:11][CH2:12][CH2:13][NH:9]5)=[N:18][CH:17]=4)=[CH:20][N:21]=3)=[CH:26][CH:27]=2)=[CH:35][N:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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 N HCl 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-8fb9b5e31a2d41d0bf562f407a5318ce
Source dataset
uspto-grants-2016_08
Patent number
US09421192B2

Reaction notes

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