Hydrochloric Acid → HCID 67505791, compound

HRID 1469609Notes

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-4d0e0ffc24364b6ab154c897a49b2d36
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006249B2

Reaction notes

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