3,5-Difluorophenylacetic acid → HCID 68607027, compound

HRID 2267657Notes

Reaction equation

HRID 2267657 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:3]1[NH:19][C:20](=[O:33])[C@H:21]([CH3:32])[NH:22]C(=O)CC1C=CC=CC=1.[F:34][C:35]1[CH:36]=[C:37]([CH2:42][C:43]([OH:45])=O)[CH:38]=[C:39]([F:41])[CH:40]=1>>[F:41][C:39]1[CH:38]=[C:37]([CH2:42][C:43]([N:19]([C@@H:3]2[C:2](=[O:1])[NH:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[S:5][C@@H:4]2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20](=[O:33])[C@H:21]([CH2:32][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:7]=2)[NH2:22])=[O:45])[CH:36]=[C:35]([F:34])[CH:40]=1

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 68606034HCID 68606034, compound

Product 1

HCID 68607027HCID 68607027, compound

Procedure

A method similar to the one described for (97) was used except that N-[(2,3-cis)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl]-L-phenylalaninamide (105a) was used as the amine component and 3,5-difluorophenylacetic acid was used as the acid component to afford the title compound as a 1:1 mixture with the 2S,3S diastereomer (58 mg), white solid, m.p. 115-120° C. 1H NMR (300 MHz, d6-DMSO) δ 4.45 (m, 1H), 4.75 (m, 1H), 5.10 (m, 1H), 6.70 (m, 2H), 6.95-7.90 (m, 16H), 8.25 (two d, 1H, J=8 Hz), 10.5 (m, 1H). MS APCI, m/z=572 (M+1). LC/MS: 2.68 min.

Sources & evidence

ORD record
ord-b5651039f1d6411e8f32a6a8b4804a68
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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