HCID 17389853, compound → HCID 67010635, compound

HRID 1630139Notes

Reaction equation

HRID 1630139 reaction equation
Cl.[CH3:2][C@@H:3]1[CH2:8][N:7]([CH2:9][C:10]([OH:12])=O)[CH2:6][C@H:5]([CH3:13])[O:4]1.[NH2:14][C@@H:15]([CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[O:17]>>[CH2:35]([O:34][CH2:33][C@H:15]([NH:14][C:10](=[O:12])[CH2:9][N:7]1[CH2:6][C@H:5]([CH3:13])[O:4][C@H:3]([CH3:2])[CH2:8]1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[O:17])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 17389853HCID 17389853, compoundHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67010635HCID 67010635, compoundYield 34.5%

Procedure

Proceeding as in Example 1, but substituting 2-((2R,6S)-2,6-dimethylmorpholino)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 234, (S)-3-(benzyloxy)-2-(2-((2R,6S)-2,6-dimethylmorpholino)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (14.8 mg, 34.5%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 7.99 (d, 1H), 7.60 (d, 2H), 7.30 (m, 5H), 7.21 (t, 2H), 7.04-6.98 (m, 4H), 4.70 (m, 1H), 4.52 (s, 2H), 3.73 (m, 2H), 3.55 (m, 2H), 2.98 (d, 2H), 2.77 (d, 1H), 2.71 (d, 1H), 1.76 (dd, 2H), 1.02 (d, 3H), 0.98 (d, 3H). MS (EI) for C30H34FN3O5. found 536.6 (MH+).

Sources & evidence

ORD record
ord-6a2886630f2f4ae88c3a950eeda6c95e
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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