Trifluoroacetic acid → HCID 178449455, compound

HRID 1611802Notes

Reaction equation

C(OC([N:8]1[CH:12]=[C:11]([CH2:13][CH:14]([C:23](=[O:48])[NH:24][CH:25]([C:41](=[O:47])[NH:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:29][CH:28]=2)[NH:15]C(OC(C)(C)C)=O)[N:10]=[CH:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:15][CH:14]([CH2:13][C:11]1[N:10]=[CH:9][NH:8][CH:12]=1)[C:23]([NH:24][CH:25]([C:41](=[O:47])[NH:42][C:43]([CH3:45])([CH3:46])[CH3:44])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][CH:32]=1)=[O:48]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of [S—(R*,R*)]-4-{2-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethylcarbamoyl]-2-tert-butoxycarbonylamino-ethyl}-imidazole-1-carboxylic acid tert-butyl ester (1.92 g, 2.87 mmol) in 70 mL dichloromethane was cooled to 3° C., then TFA (14 mL) was added. The resulting solution was warmed to 25° C. and stirred 2 hours. The mixture was concentrated at reduced pressure to a viscous amber oil which was dissolved in 100 mL ethyl acetate and washed twice with 100 mL saturated aqueous sodium bicarbonate solution and twice with 100 mL brine, dried over anhydrous sodium sulfate, and concentrated at reduced pressure affording 1.18 g (85%) of the title compound.

Workup

concentrationThe mixture was concentrated at reduced pressure to a viscous amber oil which
dissolutionwas dissolved in 100 mL ethyl acetate
washwashed twice with 100 mL saturated aqueous sodium bicarbonate solution and twice with 100 mL brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated at reduced pressure

Sources & evidence

ORD record: ord-5120059afba6446aad63b91ebe013bd6
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989448B2

Reaction notes

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