Thionyl Chloride → 4-Stearoyloxy-butyroyl chloride

HRID 990012Notes

Reaction equation

HRID 990012 reaction equation
C(OC(N[C@H](C(OC[CH:20]([CH2:25][O:26][C:27](=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:21][C:22](O)=[O:23])=O)C(C)C)=O)C1C=CC=CC=1.S(Cl)([Cl:48])=O>>[C:27]([O:26][CH2:25][CH2:20][CH2:21][C:22]([Cl:48])=[O:23])(=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 233875293-(N-benzyloxycarbonyl-L-valyloxymethyl)-4stearoyloxy-butyric acid

Product 1

HCID 867585404-Stearoyloxy-butyroyl chloride

Procedure

3-(N-benzyloxycarbonyl-L-valyloxymethyl)-4-stearoyloxy-butyric acid (1.26 g, 2 mmol), was treated with thionyl chloride (50 ml) at 35° C. for 3 hr, evaporated and coevaporated to give the product 3-N-benzyloxycarbonyl-L-valyloxy)-4-stearoyloxy-butyroyl chloride (1.3 g).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-f1c1064e37f941c7a73eff3ab995a74f
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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