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

HRID 1045837Notes

Reaction equation

HRID 1045837 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-580235a0c574466298b0ffaade37d19c
Source dataset
uspto-grants-2013_10
Patent number
US08569307B2

Reaction notes

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