Diethylamine → (R)-methyl 2-amino-3-(tritylthio)propanoate

HRID 1698200

Reaction equation

HRID 1698200 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:24]([O:26][CH3:27])=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(NCC)C>C(#N)C>[NH2:1][C@H:2]([C:24]([O:26][CH3:27])=[O:25])[CH2:3][S:4][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 59278482Fmoc-Cys(Trt)-OMe

Product 1

HCID 10429690(R)-methyl 2-amino-3-(tritylthio)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Fmoc-L-Cys(Trt)-OMe (2.58 g, 4.30 mmol) in acetonitrile (20.0 mL) was added diethylamine (20.0 mL). After 30 minutes, the mixture was concentrated in vacuo. The residue was dissolved in acetonitrile (3×10 mL) and concentrated in vacuo to afford L-Cys(Trt)-OMe as crude product which was used without purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in acetonitrile (3×10 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a433c02d64842769c4cd51537a61106
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Linked notes

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