Triethylamine → (R)-2-BOC-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid methyl ester

HRID 336451Notes

Reaction equation

HRID 336451 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([NH2:16])[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.CCN(CC)CC.[O:25](C(OC(C)(C)C)=O)[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C@@:4]([NH2:16])([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:25])[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 14390800(R)-2-Amino-3-(4-methoxy-benzylsulfanyl)propionic acid methyl ester

Product 1

HCID 68484842(R)-2-BOC-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid methyl ester (30.7 g, 127.3 mmol) prepared in Step A was dissolved in DCM. Et3N (26.4 g, 190 mmol) and (BOC)2O (27.7 g, 127.3 mmol) were added thereto, and the mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove DCM, and was used in the next reaction without further purification.

Workup

  1. customAfter completion of the reaction
  2. distillationthe reaction mixture was distilled under reduced pressure
  3. customto remove DCM
  4. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-d4520e68949e4da285d109127fd2f6f5
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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