Triethylamine → HCID 54046637, compound

HRID 1110855Notes

Reaction equation

HRID 1110855 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([CH2:7][S:8][CH2:9][C@@H:10]([NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:6])[CH3:2].[C:30]([O:34][C:35](=[O:39])[CH:36](Br)[CH3:37])([CH3:33])([CH3:32])[CH3:31].C(N(CC)CC)C>CN(P(N(C)C)(N(C)C)=O)C>[C:30]([O:34][C:35](=[O:39])[C@H:36]([CH3:37])[NH:6][C@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:29])[CH2:7][S:8][CH2:9][C@@H:10]([NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 545327tert-Butyl 2-bromopropanoateHCID 53779523HCID 53779523, compound

Product 1

HCID 54046637HCID 54046637, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A 46 g quantity of S-[(S)-2-benzyloxycarbonylamino-3-phenylpropyl]-L-cysteine ethyl ester and 27 g of 2-bromopropionic acid t-butyl ester were dissolved in 150 ml of HMPA. To the solution was added 18 ml of triethylamine and the mixture was stirred at room temperature for 48 hours. The reaction mixture was poured into ice water and the mixture was extracted with ethyl acetate. The extract was washed with water and with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure and the residue was separated and purified by silica gel column chromatography (a 5:4 mixture of ether and n-hexane as an eluent), giving the α-isomer of the title compound as a colorless oil from the first eluate. Yield 10.6 g.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was separated
  6. custompurified by silica gel column chromatography (
  7. additiona 5:4 mixture of ether and n-hexane as an eluent),

Sources & evidence

ORD record
ord-e0e6d3ca7ab94c318f6d204ead4197d0
Source dataset
uspto-grants-1990_12
Patent number
US04977179

Reaction notes

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