Boc-L-methionine → (S)-1-(3-Bromo-7-tert-butoxynaphthalen-1-yl)-3-(tert-butoxycarbonylamino)-2-oxopyrrolidine

HRID 2306239Notes

Reaction equation

HRID 2306239 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=2)[CH:5]=[C:4]([Br:17])[CH:3]=1.C(OC1C=C(C=CC=1)CN)C1C=CC=CC=1.[C:34]([O:38][C:39]([NH:41][C@H:42]([C:47](O)=[O:48])[CH2:43][CH2:44]SC)=[O:40])([CH3:37])([CH3:36])[CH3:35]>>[Br:17][C:4]1[CH:3]=[C:2]([N:1]2[CH2:44][CH2:43][C@H:42]([NH:41][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[C:47]2=[O:48])[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[C:9]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH:10]=2

Participants

4

Reactant 3

HCID 89857Boc-L-methionineHCID 11009288(3-(Benzyloxy)phenyl)methanamineHCID 184335861-Amino-3-bromo-7-tert-butoxynaphthalene

Product 1

HCID 70171503(S)-1-(3-Bromo-7-tert-butoxynaphthalen-1-yl)-3-(tert-butoxycarbonylamino)-2-oxopyrrolidine

Procedure

Following the procedures described in Example 1, Steps J-L, but using 1-amino-3-bromo-7-tert-butoxynaphthalene, as described in Example 46, Step H, in place of 3-benzyloxybenzylamine, and (S)-N-(tert-butoxycarbonyl)methionine in place of (R)-N-(tert-butoxycarbonyl)methionine in Step J, the above-titled compound was obtained.

Sources & evidence

ORD record
ord-890e69a45e1a44e7bd0757e501fb6c43
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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