Methyl chloroformate → HCID 53786906, compound

HRID 2225748Notes

Reaction equation

HRID 2225748 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:26])[C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1)=[O:14].[CH2:27](N(CC)CC)C.ClC(OC)=O>ClCCl.O>[CH3:27][O:24][C:23](=[O:25])[C:22](=[O:26])[C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 19004485HCID 19004485, compound

Product 1

HCID 53786906HCID 53786906, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[[2-(2-naphthalenyloxy)acetyl]amino]-alpha-oxobenzeneacetic acid (3.0 g) in dichloromethane (50 mL) and triethylamine (2.1 g ) was stirred at 0° C. and treated with methyl chloroformate (1.16 mL). The mixture was stirred for one hour and diluted with water, extracted with dichloromethane, dried (Na2SO4), filtered and evaporated. The residue was crystallized from dichloromethane-hexane to give 2.2 g of 4-[[2-(2-naphthalenyloxy) acetyl]amino]-alpha-oxobenzeneacetic acid methyl ester, mp 175°-176° C.

Workup

  1. stirringThe mixture was stirred for one hour
  2. extractionextracted with dichloromethane
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-628a82fa5391444d8eeb7275b8812bc1
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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