Citric Acid → HCID 14656853, compound

HRID 654306Notes

Reaction equation

HRID 654306 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:10]([OH:17])/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C@H:10]([O:17][S:35]([CH3:34])(=[O:37])=[O:36])/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 14841712HCID 14841712, compound

Product 1

HCID 14656853HCID 14656853, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.44 g (1.3 mmol) of the resultant compound of Example 6 and 0.91 ml (5.2 mmol) of diisopropylethylamine in 20 ml of anhydrous dichloromethane was cooled under N2 atmosphere to -20° C. and treated with 0.2 ml (2.6 mmol) of methanesulfonyl chloride. After 20 minutes, the mixture was treated with 10 % aqueous citric acid, extracted with methylene chloride, dried over sodium sulfate and concentrated in vacuo. Silica gel chromatography provided the desired product. 1H NMR (CDCl3) δ 1.36 (s, 9 H), 2.73 (m, 1 H), 2.93 (dd, J=14, 5 Hz, 1 H), 3.06 (S, 3 H), 3.77 (s, 3 H), 4.18 (m, 1 H), 4.62 (s, 1 H), 5.47 (m, 1 H), 6.17 (dd, J=16, 2 Hz, 1 H), 6.90 (dd, J=16, 6 Hz, 1 H), 7.15-7.35 (m, 5 H).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28b4f75d4636421486d09fb46cf249a0
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

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