Benzenamine, 4-(4-fluorophenoxy)- → (S)-benzyl 4-amino-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate

HRID 1630058Notes

Reaction equation

HRID 1630058 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][C@H:30]([NH:34]C(OC(C)(C)C)=O)[C:31](O)=[O:32])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[NH2:34][C@H:30]([C:31]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)=[O:32])[CH2:29][CH2:28][CH2:27][NH:26][C:24](=[O:25])[O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 147633Benzenamine, 4-(4-fluorophenoxy)-HCID 7269338(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

Product 1

HCID 86659466(S)-benzyl 4-amino-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamateYield 80%

Procedure

Proceeding as in Reference 5, but substituting 4-(4-fluorophenoxy)aniline and (S)-5-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)pentanoic acid, gave (S)-benzyl 4-amino-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate (1901 mg, 80%).

Sources & evidence

ORD record
ord-d91d3ddb393c48bb89ca1d68a4a37ec0
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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