L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- → HCID 67009181, compound

HRID 1630057Notes

Reaction equation

HRID 1630057 reaction equation
[Br:1][C:2]1[S:6][C:5]([O:7][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)=[N:4][CH:3]=1.[CH2:15]([O:22][CH2:23][C@H:24]([NH:28]C(OC(C)(C)C)=O)[C:25](O)=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[NH2:28][C@@H:24]([CH2:23][O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:25]([NH:12][C:11]1[CH:13]=[CH:14][C:8]([O:7][C:5]2[S:6][C:2]([Br:1])=[CH:3][N:4]=2)=[CH:9][CH:10]=1)=[O:26]

Participants

3

Reactant 2

HCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 58523210HCID 58523210, compound

Product 1

HCID 67009181HCID 67009181, compoundYield 20%

Procedure

Proceeding as in Reference 5, but substituting 4-(5-bromothiazol-2-yloxy)aniline and (S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid, gave (S)-2-amino-3-(benzyloxy)-N-(4-(5-bromothiazol-2-yloxy)phenyl)propanamide (200 mg, 20%).

Sources & evidence

ORD record
ord-4e6f729f171140809e8a88adc4e1fb41
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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