tert-Butyl isocyanate → HCID 22864456, compound

HRID 1379402Notes

Reaction equation

HRID 1379402 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]([N:27]=[C:28]=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl>[C:23]([NH:27][C:28]([NH:1][C@H:2]([C@@H:10]([OH:22])[C@@H:11]([OH:21])[C@@H:12]([NH:20][C:28]([NH: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)[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

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 15024277HCID 15024277, compound

Product 1

HCID 22864456HCID 22864456, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 30 mg (0.1 mmol) of (2S,3R,4S,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane in 1 ml of dichloromethane was treated with 25 μl (0.22 mmol) of t-butylisocyanate. The resulting solution was stirred at ambient temperature, diluted with dichloromethane, washed with brine, dried over Na2SO4, and concentrated in vacuo. Silica gel chromatography using a gradient of 1-3% methanol in chloroform provided 49 mg (98%) of the desired compound (Rf 0.4, 10% methanol in chloroform) as a white solid, m.p. 193°-196° C. Mass spectrum: (M+H)+ =499.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a3b2a71d32f43d593ca8252338cdd0f
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

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