L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- → HCID 67010062, compound

HRID 1630063Notes

Reaction equation

HRID 1630063 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([CH3:14])[CH:8]=2)=[CH:4][CH:3]=1.[CH2:17]([O:24][CH2:25][C@H:26]([NH:30]C(OC(C)(C)C)=O)[C:27](O)=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[NH2:30][C@@H:26]([CH2:25][O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:27]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([O:6][C:5]2[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:8][C:9]=1[CH3:14])=[O:28]

Participants

3

Reactant 2

HCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 26190330HCID 26190330, compound

Product 1

HCID 67010062HCID 67010062, compoundYield 58%

Procedure

Proceeding as in Reference 5, but substituting 4-(4-fluorophenoxy)-2-methylaniline and (S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid, gave (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)-2-methylphenyl)propanamide (613 mg, 58%).

Sources & evidence

ORD record
ord-ce10af00cc0d42b0ad572874ba2c1586
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…