Triethylamine → HCID 21109977, compound

HRID 1789897Notes

Reaction equation

HRID 1789897 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11](=[O:20])[NH:12][C@H:13]1[CH2:17][C@@H:16]([CH2:18][OH:19])[CH:15]=[CH:14]1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[C:6]([O:10][C:11]([NH:12][C@@H:13]1[CH2:17][C@H:16]([CH2:18][O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH:15]=[CH:14]1)=[O:20])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18453470HCID 18453470, compound

Product 1

HCID 21109977HCID 21109977, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.76 mL, 9.8 mmol) was added to a solution of cis-(4-hydroxymethyl-cyclopent-2-enyl)-carbamic acid tert-butyl ester (2 g, 9.4 mmol) and triethyl amine (1.96 mL,14.1 mmol) in CH2Cl2 (30 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. After filtration CH2Cl2 was added, and the organic phase was washed with 1M HCl, dried and concentrated under reduced pressure to yield of cis- methanesulfonic acid 4-tert-butoxycarbonylamino-cyclopent-2enylmethyl ester (2.64 g, 96%).

Workup

  1. filtrationAfter filtration CH2Cl2
  2. additionwas added
  3. washthe organic phase was washed with 1M HCl
  4. customdried
  5. concentrationconcentrated under reduced pressure to yield of cis- methanesulfonic acid 4-tert-butoxycarbonylamino-cyclopent-2enylmethyl ester (2.64 g, 96%)

Sources & evidence

ORD record
ord-5e86e143ec844908803c2782f948e0a9
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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