N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine → Fmoc-L-cysteine

HRID 1243281

Reaction equation

HRID 1243281 reaction equation
[C:1]([NH:18][C@H:19]([C:41]([OH:43])=[O:42])[CH2:20][S:21]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]>C(Cl)Cl>[C:1]([NH:18][C@H:19]([C:41]([OH:43])=[O:42])[CH2:20][SH:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Participants

3

Reactant 1

HCID 128239N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine

Product 1

HCID 11024349Fmoc-L-cysteineYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Fmoc-S-trityl-L-cysteine (10.0 g, 17.1 mmol), in DCM containing 15% trifluoroacetic acid (TFA) and 5% TES (total volume 150 mL) was stirred at room temperature. After 10 min the reaction was evaporated to dryness, the solid residue was washed three times with 150 mL n-pentane and then dried under high vacuum. 4.46 g of Fmoc-L-cysteine was obtained as a colorless solid. This material was dissolved in DCM (20 mL) containing 7% TFA. 1.0 g Trityl chloride resin (Novabiochem, loading 2.05 mmol of active chlorine) was added in one portion. The solution was slowly agitated overnight (orbital shaker, or slow stirring on a magnetic stirrer). The resin was isolated on a sintered glass funnel, washed with DCM (5×40 mL), methanol (1×40 mL) and again with DCM and dried overnight in vacuo.

Workup

  1. customAfter 10 min the reaction was evaporated to dryness
  2. washthe solid residue was washed three times with 150 mL n-pentane
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-042c8c9670cb4cb690341602466a45b4
Source dataset
uspto-grants-2006_10
Patent number
US07119073B2

Linked notes

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