Di-tert-butyl dicarbonate → HCID 57239987, compound

HRID 847638Notes

Reaction equation

HRID 847638 reaction equation
[NH2:1][C@H:2]([C@H:10]([OH:22])[C@H:11]([OH:21])[C@@H:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:23]([O:27][C:28](O[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl>[NH2:1][C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C@@H:10]([OH:22])[C@@H:11]([OH:21])[C@@H:12]([NH:20][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:23]([O:27][C:28]([NH:1][CH:2]([CH:10]([OH:22])[CH:11]([OH:21])[CH:12]([NH:20][C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 15024277HCID 15024277, compound

Product 2

HCID 3011028HCID 3011028, compoundYield 20%HCID 57239987HCID 57239987, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 200 mg (0.67 mmol) of (2S,3S,4R,5S)-2,5-diamino-3,4-dihydroxy1,6-diphenylhexane in 10 ml of dichloromethane was treated with 174 mg (0.8 mmol) of di-t-butyldicarbonate. After being allowed to stir overnight at ambient temperature, the solution was concentrated, and the residue was purified by silica gel chromatography using 10% methanol in chloroform to provide 180 mg (56%) of the desired compound along with 80 mg (20%) of the resultant compound of Example 206.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5c9cf090fe56433980a984e535844bee
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

Loading…