Potassium Carbonate → HCID 69545867, compound

HRID 2086264Notes

Reaction equation

HRID 2086264 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][NH:8][S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].Br[CH2:25]/[CH:26]=[CH:27]/[C:28]([O:30][CH3:31])=[O:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([CH2:7][N:8]([S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])[CH2:25][CH:26]=[CH:27][C:28]([O:30][CH3:31])=[O:29])=[O:23])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 22727149HCID 22727149, compound

Product 1

HCID 69545867HCID 69545867, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (6-chloro-naphthalene-2-sulfonyl)glycine tert-butyl ester (17.79 g), methyl 4-bromocrotonate (13.426 g) and potassium carbonate (8.28 g) in DMF (150 ml) was stirred at 50° C. for 1 hour. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate, washed with water and brine, dried and concentrated to obtain a residue, which was crystallized from ether to obtain methyl 4-[(tert-butoxycarbonylmethyl)(6-chloro-naphthalene-2-sulfonyl)amino]-2-butenoate (25.13 g) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customto obtain a residue, which
  7. customwas crystallized from ether

Sources & evidence

ORD record
ord-8ab1bb8e9cb5480ba87f6d9c9cb59251
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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