Dichloromethane → HCID 54080242, compound

HRID 1855695Notes

Reaction equation

HRID 1855695 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]([OH:9])[CH2:6][O:7][CH3:8].C(Cl)Cl.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>CO>[CH3:1][O:2][C:3](=[O:14])[C:4]([NH:10][C:11](=[O:13])[CH3:12])=[C:5]([O:9][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:6][O:7][CH3:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54300732HCID 54300732, compound

Product 1

HCID 54080242HCID 54080242, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution consisting of 20.5 g (0.1 mol) of alcohol 8, 1 l of methylene chloride, and 20.5 ml of triethylamine was cooled to 0° under an argon atmosphere. Methanesulfonyl chloride (8.5 ml) was added dropwise with stirring. The resultant solution was maintained at 0° for 1/2 hr. Methanol (0.4 ml) was added, and the solvent was removed in vacuo (35°). The white solid residue was triturated with ethyl acetate and the extract filtered through a column containing silica gel (200 g). The fractions containing product (as determined by thin layer chromatography) were concentrated in vacuo yielding 2-acetamido-3-mesyloxy-4-methoxy-butenoic acid methyl ester (9) as a partially crystalline residue. Crystallization from ethyl acetate/petroleum ether (bp 35°-60°) gave one of the diastereomers as a white crystalline solid: mp 101.5°-104.5°; NMR (CDCl3) δ 6.4 (broad d, 1H, NH), 5.2 (m, 1H, CH2CH), 5.0 (m, 1H, CHNH), 3.8 (s, 3H, CH3O2C--), 3.6 (m, 2H, CH3OCH2 --), 3.3 (s, 3H, CH3OCH2 --), 3.0 (s, 3H, CH3SO 3 --), 2.0 (s, 3H, CH3CONH--). (Calcd. for C9H17NO7S: C, 38.16; H, 6.05; N, 4.94; S, 11.31. Found: C, 38.34; H, 6.21; N, 4.92; S, 11.27).

Workup

  1. temperaturewas cooled to 0° under an argon atmosphere
  2. customthe solvent was removed in vacuo (35°)
  3. customThe white solid residue was triturated with ethyl acetate
  4. filtrationthe extract filtered through a column
  5. additioncontaining silica gel (200 g)
  6. additionThe fractions containing product (as determined by thin layer chromatography)
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-bbc9639881bf48119c71e7afa2e4cb93
Source dataset
uspto-grants-1980_08
Patent number
US04216008

Reaction notes

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