Diisopropylethylamine → HCID 11362797, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Glycine tert-butyl ester hydrochloride	HCID 2725036	—
Reactant	5-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride	HCID 2735713	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 11362797	HCID 11362797	63%

Reaction Steps

H-Gly-OtBu.HCl (263 mg, 1.57 mmol) is dissolved in 20 ml CH2Cl2. pH is adjusted to 9 using i-Pr2NEt as a base (537 μl, 3.14 mmol). To this solution is added dropwise 1b (500 mg, 1.43 mmol) in 10 ml DMF. The reaction is stirred overnight. 30 ml of CH2Cl2 are added and the organic phase washed with HCl (0.1N) and sat. NaCl sol. Drying over MgSO4 and evaporating the solvent to dryness affords 1c (400 mg, 63%) as a white solid. mp °C., 1H NMR (d6-DMSO) δ 9.34 (t, J=6.40 Hz, 1H), 8.25 (t, J=6.40 Hz, 1H), 7.89 (d, J=8.67 Hz, 2H), 7.56 (d, J=8.67 Hz, 2H), 7.41 (d, J=3.77 Hz, 1H), 7.05 (d, J=3.7 Hz, 1H), 4.62 (d, J=6.40 Hz, 2H), 3.59 (d, J=6.40 Hz, 2H), 1.3 (s, 9H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07638538B1
Source dataset	uspto-grants-2009_12
ORD ID	ord-e0831879cd60448bac8e0121badc80f8
Source note	uspto-grants-2009_12