Trityl chloride → HCID 21144450, compound

HRID 242767Notes

Reaction equation

HRID 242767 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][SH:9])[NH2:7])[CH3:3].[C:11](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([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>CN(C=O)C>[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][S:9][C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:7])[CH3:3]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 2723617Ethyl cysteinate hydrochloride

Product 1

HCID 21144450HCID 21144450, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Cysteine ethyl ester hydrochloride (5.0 g, 27.03 mmol, 1 eq.) and trityl chloride (11.3 g, 40.55 mmol, 1.5 eq) were stirred in 20 mL of DMF for 2 days at room temperature. The reaction was purified by direct injection into RP-HPLC using 50-100% water/acetonirile gradient (no TFA added) over 20 min. After drying in vacuo, 9.3 g (88%) of 203 was obtained as a white powder. 1H NMR (500 MHz, CD3OD): δ=7.23-7.41 (m, 15H), 4.18 (q, 2H, J=7.5 Hz), 3.17 (m, 1H), 2.58 (dd, 1H, J=8.5 Hz, 12 Hz), 2.48 (dd, 1H, J=5 Hz, 12 Hz), 1.35 (t, 3H, J=7.5 Hz). 13C NMR (125 MHz, CD3OD) δ 171.9, 145.9, 130.7, 129.0, 127.9, 68.1, 62.5, 53.3, 30.8, 14.3. EI-MS (m/z): [M+1] calculated for C24H27NO2S 392.2. found 393.2.

Workup

  1. customThe reaction was purified by direct injection into RP-HPLC
  2. additionadded) over 20 min
  3. customAfter drying in vacuo

Sources & evidence

ORD record
ord-d584ec1a6d9b4ed8bee9b052cf640231
Source dataset
uspto-grants-2014_02
Patent number
US08653238B2

Reaction notes

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