Triethylamine → HCID 69413992, compound

HRID 856908Notes

Reaction equation

HRID 856908 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][SH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH2:20]([O:19][C:17]([CH2:16][S:11][CH2:10][C@@H:9]([C:12]([OH:14])=[O:13])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62576Benzyl bromoacetateHCID 152319N-tert-Butyloxycarbonylcysteine

Product 1

HCID 69413992HCID 69413992, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(tert-Butyloxycarbonyl)-L-cysteine (3.5 g, 15.8 mmol), benzyl 2-bromoacetate (3.7 g, 16.1 mmol) and triethylamine (1.8 g, 18.0 mmol) were dissolved in THF (100 ml). The mixture was stirred for 18 hours at room temperature then diluted with ethyl acetate (100 ml), washed with 0.3M KHSO4, sat NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (eluant: 95% chloroform, 4% methanol, 1% acetic acid) to give a colourless oil identified as S-(benzyloxyrarbonylmethyl)-N-(tert-butyloxycarbonyl)-L-cysteine (5.2 g, 14.1 mmol, 89%).

Workup

  1. washwashed with 0.3M KHSO4
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (eluant: 95% chloroform, 4% methanol, 1% acetic acid)
  5. customto give a colourless oil

Sources & evidence

ORD record
ord-257e291744bd4eb99c123504f20bbc0a
Source dataset
uspto-grants-2006_12
Patent number
US07144886B2

Reaction notes

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