Triethylamine → HCID 67924837, compound

HRID 727794Notes

Reaction equation

HRID 727794 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C(N(CC)CC)C.[NH2:19][CH:20]([NH2:38])[C@@H:21]([OH:37])[C@@H:22]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCl>[C:30]([C@@H:22]([CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C@H:21]([OH:37])[C:20]([NH2:38])([NH2:19])[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])([O:32][C:33]([CH3:35])([CH3:36])[CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 67924832HCID 67924832, compound

Product 1

HCID 67924837HCID 67924837, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.18 ml of benzyl chloroformate are added at a temperature of 2° to 5° to a solution of 5.28 ml of triethylamine and 6.3 g of (2S,3S)-1-amino-3-BOC-amino-4-cyclohexyl-2-butanol in 120 ml of dichloromethane, and the solution obtained is stirred for 30 minutes at room temperature. The solution is then diluted with dichloromethane and washed with 0.25N hydrochloric acid, saturated aqueous sodium bicarbonate solution and water. The organic phase is dried over sodium sulphate and evaporated under vacuum. Chromatography of the residue on silica gel using toluene/ethyl acetate (3:1) as the eluant yields (2S,3S)-3-BOC-amino-1-Cbz-amino-4-cyclohexyl-2-butanol as a slightly yellowish oil.

Workup

  1. customthe solution obtained
  2. washwashed with 0.25N hydrochloric acid, saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-e1ca9e5844454b789ea98cef3030dd0e
Source dataset
uspto-grants-1991_09
Patent number
US05045537

Reaction notes

Loading…