Hydrochloric Acid → HCID 86644348, compound

HRID 1515238Notes

Reaction equation

HRID 1515238 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C@H:5]([NH2:17])[CH2:6][CH:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][OH:9])[CH3:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>ClCCl>[CH2:1]([O:3][C:4](=[O:18])[C@H:5]([NH2:17])[CH2:6][CH:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:8][O:9][S:27]([CH3:26])(=[O:29])=[O:28])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86644349HCID 86644349, compound

Product 1

HCID 86644348HCID 86644348, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-4-BOC-amino-5-hydroxy-pentanoic acid ethyl ester (36 g, 137.8 mmol) prepared in Step A and triethylamine (38.4 mL, 275.5 mmol) were dissolved in dichloromethane (200 mL). Methanesulfonylchloride (11.7 mL, 151.5 mmol) was added in drops thereto, and the mixture was stirred for 1 h at 0° to room temperature. After completion of the reaction, 1N hydrochloric acid solution was added, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate to give the title compound.

Workup

  1. additionwas added
  2. extractionwhich was then extracted with ethyl acetate
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-e0b8b26b65c947d79590a9720525d41e
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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