Triethylamine → HCID 23519194, compound

HRID 1836603Notes

Reaction equation

HRID 1836603 reaction equation
[C:1]([NH:8][C:9]([CH3:14])([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH2:16]([O:18][C:19](=[O:31])[C@H:20]([CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:21])[CH3:17].C(N=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[CH2:16]([O:18][C:19](=[O:31])[C@H:20]([CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:21][C:11](=[O:13])[C:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])([CH3:10])[CH3:14])[CH3:17]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 13500733HCID 13500733, compound

Product 1

HCID 23519194HCID 23519194, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of BOC-α-methylalanine (3.05 g, 15 mmol), O-benzyl-L-serine ethyl ester hydrochloride (3.89 g, 15 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCl, 2.88 g, 15 mmol) and 1-hydroxy-7-azabenzotriazole (HOAT, 2.04, 15 mmol) in methylene chloride (150 mL) is added triethylamine (1.52 g, 15 mmol). The mixture is stirred overnight and then concentrated in vacuo. The residue is re-dissolved in ethyl acetate and washed with water, 1 N HCl, water, and brine. The solution is dried over sodium sulfate and concentrated to yield N-[2-(BOC-amino)-2-methylpropionyl]-O-benzyl-L-serine ethyl ester of the formula

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is re-dissolved in ethyl acetate
  3. washwashed with water, 1 N HCl, water, and brine
  4. dry with materialThe solution is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0b0a71ea5ff24f8d842c5740d105fbae
Source dataset
uspto-grants-2004_08
Patent number
US06777443B2

Reaction notes

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