Water → HCID 66704595, compound

HRID 426057Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[CH2:6][CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC.Cl[C:32]([O:34][CH3:35])=[O:33].O>C(Cl)Cl>[CH3:35][O:34][C:32]([NH:1][CH2:2][CH2:3][CH2:4][N:5]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[CH2:6][CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:33]

Participants

Conditions

Temperature: 2.5 °C

Procedure

To a solution of tert-butyl 2-((3-aminopropyl)(3-chlorophenyl)amino)ethyl(methyl)carbamate (300 mg, 0.88 mmol) in dry CH2Cl2 (5 mL), Et3N (583 mg, 5.3 mmol) was added. The resulting mixture was cooled to 0-5° C. and a solution of methyl chloroformate (965 mg, 10.3 mmol, 5 eq) in dry CH2Cl2 (5 mL) was added dropwise. After addition, the reaction mixture was stirred for 1-2 h at 0-5° C. Upon completion of the reaction, water (10 mL) was added, the aqueous layer was extracted with CH2Cl2 (3×8 mL), the combined organic layers were washed with 10% citric acid (2×5 mL) and brine, then dried over Na2SO4. The filtrate was concentrated to the crude product which was purified by preparative HPLC to tert-butyl 2-((3-(methoxycarbonylamino)propyl)(3-chlorophenyl)amino)ethyl(methyl)carbamate (200 mg, yield 83%).

Workup

additionAfter addition
additionwas added
extractionthe aqueous layer was extracted with CH2Cl2 (3×8 mL)
washthe combined organic layers were washed with 10% citric acid (2×5 mL) and brine
dry with materialdried over Na2SO4
concentrationThe filtrate was concentrated to the crude product which

Sources & evidence

ORD record: ord-137bccf8314e49d29a2bdc06887523e7
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106221B2

Reaction notes

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