Citric Acid → HCID 56993776, compound

HRID 1018913Notes

Reaction equation

HRID 1018913 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([S:20][CH2:21][C@@H:22]([C:24]([OH:26])=[O:25])[NH2:23])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1[S:45](Cl)(=[O:47])=[O:46].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1[S:45]([NH:23][C@H:22]([C:24]([OH:26])=[O:25])[CH2:21][S:20][C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=1)(=[O:46])=[O:47]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 71252-Naphthalenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 7472794HCID 7472794, compound

Product 1

HCID 56993776HCID 56993776, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred mixture of commercially available S-4-monomethoxytrityl-(L)-cysteine (11) (0.34 g, 1 mmol), dioxane (5 mL) and 10% aqueous sodium carbonate (5 mL) was added 2-naphtalenesulfonyl chloride (0.25 g, 1.1 mmol). After stirring for 1 h, the reaction mixture was acidified by addition of 5% aqueous citric acid (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried (magnesium sulfate) and concentrated under reduced pressure. The crude product was chromatographed on silica gel (methanol/dichloromethane/triethylamine, 0/99/1 to 4/95/1, v/v/v) to yield 12 (76% yield, 0.44 g).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was chromatographed on silica gel (methanol/dichloromethane/triethylamine, 0/99/1 to 4/95/1, v/v/v)

Sources & evidence

ORD record
ord-fb2cc8a1fb0a4bb6b3c4c3381ccffb05
Source dataset
uspto-grants-2002_11
Patent number
US06486129B1

Reaction notes

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