Hydrochloric Acid → 2-tert-Butoxycarbonylamino-3-methylsulfonylpropanoic acid methyl ester

HRID 900376Notes

Reaction equation

HRID 900376 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15](N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].Cl>ClCCl>[CH3:15][O:14][C:12](=[O:13])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][S:23]([CH3:22])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 866053502-tert-Butoxycarbonylamino-3-methylsulfonylpropanoic acid methyl esterYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-tert-butoxycarbonylserine (1.1 g, 5.0 mmol) and triethylamine (0.84 mL, 6.0 mmol) in dichloromethane (50 mL) was cooled to 0° C. and treated with methylsulfonyl chloride (0.44 mL, 5.8 mmol)). After stirring an additional 2 h, the reaction mixture was acidified with 2% HCl (20 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were washed successively with sat. aq NaHCO3, and sat. aq NaCl, dried over MgSO4 and concentrated. Purification by flash column chromatography (5% ethyl acetate in heptane) gave the desired product (1.25 g, 84%) as an oil. 1H NMR (CDCl3), 5.71 (d, J=7 Hz, 1H), 4.56 (m, 3H), 3.82 (s, 3H), 3.02 (s, 3H), 1.44 (s, 9H).

Workup

  1. extractionextracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers were washed successively with sat. aq NaHCO3, and sat. aq NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (5% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f4c75b9381e14ca4942ad6d1b503f5c3
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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