Water → HCID 90060382, compound

HRID 1779238Notes

Reaction equation

[F:1][C:2]([F:50])([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[C@H:11]([C:21](=[O:42])[NH:22][C@H:23]([C:38]([O:40]C)=[O:39])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])=[CH:27][CH:26]=1)[C@@:12]([OH:20])([CH2:16][CH2:17][O:18][CH3:19])[C:13]([OH:15])=[O:14].O.C(N(CC)CC)C.[Br-].[Li+]>C(#N)C>[C:38]([C@@H:23]([NH:22][C:21]([C@@H:11](/[CH:10]=[CH:9]/[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:50])([F:1])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C@@:12]([OH:20])([CH2:16][CH2:17][O:18][CH3:19])[C:13]([OH:15])=[O:14])=[O:42])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])=[CH:27][CH:26]=1)([OH:40])=[O:39]

Participants

Conditions

Temperature: 50 °C

Procedure

No. 5538573, (E)-(2S,3S)-12,12-difluoro-3-[(S)-2-(2′-fluoro-biphenyl-4-yl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid (8.2 mg, 0.0116 mmol) was dissolved in acetonitrile (0.328 mL), and water (0.0011 mL, 0.0611 mmol), triethylamine (0.0097 mL, 0.0696 mmol), and anhydrous lithium bromide (20.1 mg, 0.231 mmol) were then added at room temperature. The reaction mixture was stirred at 50° C. for 3.5 hours, cooled to room temperature, and then purified by preparative HPLC to obtain 6.7 mg of the title compound (0.00969 mmol, 83% yield).

Workup

temperaturecooled to room temperature
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-c9a5c944820d4e03b2c473024d7cd0cb
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266853B2

Reaction notes

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