Triethylamine → HCID 131723213, compound

HRID 8849Notes

Reaction equation

Cl[S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:4])=[O:3].[C:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].CCN(CC)CC>C(Cl)Cl>[C:21]([O:20][C:18]([N:25]1[CH2:30][CH2:29][N:28]([S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])(=[O:4])=[O:3])[CH2:27][CH2:26]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet was charged with 5.2 g benzyl 3-chlorosulfonyl-2(R)-methylpropionate in 50 mL CH2Cl2. The flask was cooled to 0° C. and charged with 3.5 g N-Boc-piperazine and 2.9 mL (1.1 eq.) NEt3. The reaction was stirred 30 minutes at 0° C., concentrated in vacuo and partitionned between ethyl acetate/water. The combined organics were washed with 5% aqueous. citric acid, saturated aqueous sodium bicarbonate, brine, and concentrated in vacuo to yield a yellow liquid. Purification via flash chromatography on silica gel (30% ethyl acetate/hexane) yielded 7.2 g (90%) product as a clear oil.

Workup

customA 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet
concentrationconcentrated in vacuo
washThe combined organics were washed with 5% aqueous
concentrationcitric acid, saturated aqueous sodium bicarbonate, brine, and concentrated in vacuo
customto yield a yellow liquid
customPurification via flash chromatography on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-bef8ec050b714bbf828863d3d57b24dd
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091219B2

Reaction notes

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