Triethylamine → HCID 23519196, compound

HRID 1612094Notes

Reaction equation

HRID 1612094 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:17])[C@H:6]([CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:7])[CH3:3].[C:18]([NH:25][C:26]([CH3:31])([C:28](O)=[O:29])[CH3:27])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:17])[C@H:6]([CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:7][C:28](=[O:29])[C:26]([NH:25][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:31])[CH3:27])[CH3:3]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 12839759Ethyl S-benzyl-(R)-cysteinate hydrochloride (1:1)

Product 1

HCID 23519196HCID 23519196, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of S-benzyl-L-cysteine ethyl ester hydrochloride (7.98 g, 29 mmol), BOC-α-methylalanine (5.89 g, 29 mmol), triethylamine (2.93 g, 29 mmol), 1-hydroxybenzotriazole (HOBT, 3.92 g, 29 mmol) and EDCI (5.57 g, 29 mmol) in methylene chloride (200 mL) is stirred under an argon atmosphere at room temperature overnight. The reaction mixture is evaporated to dryness and the residue is dissolved in ethyl acetate (200 mL). The solution is washed with water (50 mL), 1 N HCl (50 mL), water (50 mL), 5% sodium bicarbonate (50 mL), water (50 mL) and finally brine (25 mL). The solution is then dried over sodium sulfate, filtered and evaporated to dryness to give N-[2-(BOC-amino)-2-methylpropionyl]-S-benzyl-L-cysteine ethyl ester.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. dissolutionthe residue is dissolved in ethyl acetate (200 mL)
  3. washThe solution is washed with water (50 mL), 1 N HCl (50 mL), water (50 mL), 5% sodium bicarbonate (50 mL), water (50 mL) and finally brine (25 mL)
  4. dry with materialThe solution is then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-3b14f83022014c22836f6c941e749c35
Source dataset
uspto-grants-2006_01
Patent number
US06992105B2

Reaction notes

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