N-(tert-butoxycarbonyl)glycine → HCID 66902308, compound

HRID 2242293Notes

Reaction equation

HRID 2242293 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:13]([O:15][C:16]([C@:18]1([NH2:30])[CH2:23][C@H:22]([OH:24])[C@@H:21]2[C@H:19]1[C@H:20]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:17])[CH3:14]>>[CH2:13]([O:15][C:16]([C@:18]1([NH:30][C:10](=[O:12])[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:23][C@H:22]([OH:24])[C@@H:21]2[C@H:19]1[C@H:20]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:17])[CH3:14]

Participants

3

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 66902392HCID 66902392, compound

Product 1

HCID 66902308HCID 66902308, compound

Procedure

Prepare according to General Procedure A using Boc-Glycine (458 mg, 2.62 mmol, Aldrich) and (1S,2S,4S,5R,6R)-2-amino-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester (450 mg, 1.75 mmol, Preparation 22). Purify on 35 g of silica eluting with a gradient from 50/50 to 20/80 hexanes/ethyl acetate. Yield: 560 mg (77%).

Workup

  1. customPrepare
  2. customPurify on 35 g of silica eluting with a gradient from 50/50 to 20/80 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-80c61ff54d3a4b02b480111c8bd2513c
Source dataset
uspto-grants-2010_03
Patent number
US07671082B2

Reaction notes

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