L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- → HCID 67010374, compound

HRID 1630049Notes

Reaction equation

HRID 1630049 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.[CH2:14]([O:21][CH2:22][C@H:23]([NH:27]C(OC(C)(C)C)=O)[C:24](O)=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[NH2:27][C@@H:23]([CH2:22][O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:24]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([O:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[CH:8][CH:9]=1)=[O:25]

Participants

3

Reactant 2

HCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 433639914-[(1,3-Thiazol-2-yl)oxy]aniline

Product 1

HCID 67010374HCID 67010374, compoundYield 60%

Procedure

Proceeding as in Reference 5, but substituting 4-(thiazol-2-yloxy)aniline and (S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid, gave (S)-2-amino-3-(benzyloxy)-N-(4-thiazol-2-yloxyphenyl)propanamide (200 mg, 60%).

Sources & evidence

ORD record
ord-e2f166bdf54c402c9c4c18c6af20a2c3
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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