Water → HCID 3637091, compound

HRID 1351137Notes

Reaction equation

C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:14])[CH2:12][NH2:13].[C:15]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1.O>ClCCl>[CH3:9][O:10][C:11](=[O:14])[CH2:12][NH:13][C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:16][CH:17]=1)=[O:22]

Participants

Conditions

Temperature: -5 °C

Procedure

Dichloromethane (50 mL) and then triethylamine (11.2 mL, 79.6 mmol, 2.0 eq) were added to glycine methyl ester hydrochloride (5.0 g, 39.8 mmol, 1.0 eq). The mixture was stirred and cooled to −5° C. using an ice/methanol bath. A suspension of biphenyl-4-carbonyl chloride (8.26 g, 39.8 mmol, 1.0 eq) in dichloromethane (25 mL) was added over 22 minutes. The mixture was stirred for 3 hours at −5° C., and then left to stir at room temperature overnight (16 hours). Water (75 mL) was added and the mixture was stirred rapidly for 30 minutes at room temperature. The layers were separated. The organic layer was washed with water (75 mL), then evaporated to dryness using a rotary evaporator to give an off-white solid (6.58 g, 62%).

Workup

additionwas added over 22 minutes
stirringThe mixture was stirred for 3 hours at −5° C.
waitleft
stirringto stir at room temperature overnight (16 hours)
stirringthe mixture was stirred rapidly for 30 minutes at room temperature
customThe layers were separated
washThe organic layer was washed with water (75 mL)
customevaporated to dryness
customa rotary evaporator

Sources & evidence

ORD record: ord-3ff8b6058a3b4907be69335a8bdcde52
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217708B2

Reaction notes

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