1158584-44-1 → HCID 67010434, compound

HRID 1630114Notes

Reaction equation

Cl.[S:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.[NH2:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15]>>[CH2:33]([O:32][CH2:31][C@H:13]([NH:12][C:9](=[O:11])[CH2:8][N:5]1[CH2:4][CH2:3][S:2][CH2:7][CH2:6]1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Reactant 2

HCID 441208531158584-44-1

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67010434HCID 67010434, compoundYield 33.9%

Procedure

Proceeding as in Example 1, but substituting 2-thiomorpholinoacetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 266, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-thiomorpholinoacetamido)propanamide (14.2 g, 33.9%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 7.96 (d, 1H), 7.60 (d, 2H), 7.28-7.34 (m, 5H), 7.19-7.23 (m, 2H), 6.98-7.04 (m, 4H), 4.68-4.69 (m, 1H), 4.52 (s, 2H), 3.70-3.77 (m, 2H), 3.01 (s, 2H), 2.67-2.73 (m, 4H), 2.60-2.63 (m, 4H). MS (EI) for C28H30FN3O4S. found 524.6 (MH+).

Sources & evidence

ORD record: ord-32499c7443fc4a7a9c5a55e809af2670
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791102B2

Reaction notes

Loading…