Hydrochloric Acid → HCID 67505791, compound

HRID 2384029Notes

Reaction equation

[C:1]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:17][C:18]([C:20]2[S:24][C:23]([C:25]([OH:27])=O)=[CH:22][CH:21]=2)=[O:19])[CH2:9][C@H:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:11])=[CH:3][CH:2]=1.C([N:37](C(C)C)CC)(C)C.ClC(OCC(C)C)=O.[OH-].[NH4+].Cl>C1COCC1>[CH2:15]([O:14][C:12](=[O:13])[C@H:10]([CH3:11])[CH2:9][C@H:8]([NH:17][C:18]([C:20]1[S:24][C:23]([C:25](=[O:27])[NH2:37])=[CH:22][CH:21]=1)=[O:19])[CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:6][CH:5]=1)[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-((1S,3R)-1-biphenyl-4-ylmethyl-3-ethoxycarbonyl-butylcarbamoyl)-thiophene-2-carboxylic acid (115 mg, 0.247 mmol) in THF (1 mL) at 0° C. is added diisopropylethylamine (63.8 mg, 0.494 mmol) followed by dropwise addition of a solution of isobutyl chloroformate (33.7 mg, 0.247 mmol) in THF (0.1 mL). The mixture is stirred at 0° C. for 30 minutes then ammonium hydroxide (0.3 mL of 14.8 M solution) is added. The mixture is allowed to warm to room temperature then aqueous 1M HCl (3 mL) is added. Most of the THF is removed under reduced pressure and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure to give (2R,4S)-5-biphenyl-4-yl-4-[(5-carbamoyl-thiophene-2-carbonyl)-amino]-2-methyl-pentanoic acid ethyl ester. MS 465.3 (M+1).

Workup

temperatureto warm to room temperature
customMost of the THF is removed under reduced pressure
extractionthe mixture is extracted with ethyl acetate
dry with materialThe organic phase is dried over sodium sulfate
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-75b03a443369432492d62a324ba30bab
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263629B2

Reaction notes

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