Hydrochloric Acid → HCID 86644348, compound

HRID 336447Notes

Reaction equation

HRID 336447 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° C. 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-18b576aab60842baab226bdb45ff9e72
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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