L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- → HCID 67009704, compound

HRID 1630062Notes

Reaction equation

HRID 1630062 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[NH2:5].[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:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:2]([Cl:1])[CH:3]=1)=[O:28]

Participants

3

Reactant 2

HCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 906443-Chloro-4-(4-chlorophenoxy)aniline

Product 1

HCID 67009704HCID 67009704, compoundYield 89%

Procedure

Proceeding as in Reference 5, but substituting 3-chloro-4-(4-chlorophenoxy)aniline and (S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid, gave (S)-2-amino-3-(benzyloxy)-N-(3-chloro-4-(4-chlorophenoxy)phenyl)propanamide (80 mg, 89%).

Sources & evidence

ORD record
ord-f477f0232a7647119b1bcd98b9ca7499
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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