Dimethylformamide → HCID 86674674, compound

HRID 1261403Notes

Reaction equation

HRID 1261403 reaction equation
[CH2:1]([O:8][C@@H:9]([CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1([S:14](O)(=[O:16])=[O:15])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.O=S(Cl)[Cl:34]>>[CH2:1]([O:8][C@@H:9]([CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1([S:14]([Cl:34])(=[O:16])=[O:15])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86674672HCID 86674672, compound

Product 1

HCID 86674674HCID 86674674, compoundYield 52%

Procedure

A mixture of (R)-1-(2,3-bis(benzyloxy)propyl)cyclopropane-1-sulfonic acid (630 g) and DMF (30 mL) in SOCl2 (1.5 L) was refluxed for 2 hours until HPLC analysis showed the reaction had gone to completion. The reaction mixture was concentrated to dryness and the residue purified on silica gel chromoatography with eluent: heptane for 5 minutes, then IPAC: heptanes=1:30; heptanes 1:10 resulting in the product as a red oil (298.5 g; 52% yield; 95% purity). 1H NMR (CDCl3, 400 MHz): δ 7.34 (m, 10H), 4.68 (d, 1H), 4.56 (bs, 1H), 4.53 (d, 1H), 4.16 (m, 1H), 3.54-3.62 (m, 2H), 2.63 (dd, 1H), 2.01 (q, 1H), 1.52-1.81 (m, 3H), 1.16 (m, 1H), 2.22 (bs, 1H), 1.75 (t, 2H), 1.38-1.40 (m, 2H).

Workup

  1. temperaturewas refluxed for 2 hours until HPLC analysis
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customthe residue purified on silica gel chromoatography with eluent

Sources & evidence

ORD record
ord-14123015363345108c24109d1cf53193
Source dataset
uspto-grants-2013_06
Patent number
US08470878B2

Reaction notes

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