N-(tert-Butoxycarbonyl)-D-prolinol → tert-butyl (S)-2-[6-bromo-3-bis-(tert-butoxycarbonyl)amino-2-methoxycarbonylphenoxy-methyl]pyrrolidine-1-carboxylate

HRID 715952Notes

Reaction equation

HRID 715952 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:6]([C:22]([O:24][CH3:25])=[O:23])[C:5]([N:26]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:4][CH:3]=1.OC[C@H]1CCCN1C(OC(C)(C)C)=O.BrC1C(O)=C(C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=CC=1)C(OC)=O>>[Br:1][C:2]1[C:7]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[C:6]([C:22]([O:24][CH3:25])=[O:23])[C:5]([N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 70983234Methyl 3-bromo-6-bis-(tert-butoxycarbonyl)amino-2-hydroxybenzoate2×HCID 71003908tert-butyl (R)-2-[6-bromo-3-bis-(tert-butoxycarbonyl)amino-2-methoxycarbonylphenoxymethyl]pyrrolidine-1-carboxylate

Product 1

HCID 71003911tert-butyl (S)-2-[6-bromo-3-bis-(tert-butoxycarbonyl)amino-2-methoxycarbonylphenoxy-methyl]pyrrolidine-1-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 8, starting from tert-butyl (R)-2-hydroxymethylpyrrolidine-1-carboxylate and methyl 3-bromo-6-bis-(tert-butoxycarbonyl)amino-2-hydroxybenzoate (Intermediate 9).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7ac7aa1d2f504c879ae7cb0ce87469a6
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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