S-Trityl-L-Cysteine → HCID 67392281, compound

HRID 907628Notes

Reaction equation

HRID 907628 reaction equation
[F:1][C:2]([F:28])([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=1)[C@H:3](OS(C(F)(F)F)(=O)=O)[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[NH2:29][C@@H:30]([CH2:34][S:35][C:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]([OH:33])=[O:32]>C(Cl)Cl>[F:28][C:2]([F:1])([O:19][C:20]1[CH:21]=[CH:22][C:23]([S:26][CH3:27])=[CH:24][CH:25]=1)[C@@H:3]([NH:29][C@@H:30]([CH2:34][S:35][C:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:31]([OH:33])=[O:32])[C:4]1[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 76044S-Trityl-L-CysteineHCID 86626346HCID 86626346, compound

Product 1

HCID 67392281HCID 67392281, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trifluoromethanesulfonic acid 2,2-difluoro-1(R)-(4-fluorophenyl)-2-(4-methylsulfanylphenoxy)ethyl ester (1.70 g, 3.8 mmol), 2(R)-amino-3-tritylsulfanylpropionic acid (1.38 g, 38 mmol) and diisiopropylethylamine (2.65 ml, 15.2 mol) in DCM (35 ml) was stirred for 19 h at room temperature. The solvent was evaporated under vacuum and the residue dissolved in ethyl ether (20 ml). The solution was washed with 1N HCl solution and brine. After drying over sodium sulfate, the solvent was evaporated and the crude was purified by flash chromatography, using a mixture of EA/H (1/3) as eluent to give 2(R)-[2,2-difluoro-1(S)-(4-fluorophenyl)-2-(4-methylsulfanylphenoxy)ethylamino]-3-tritylsulfanylpropionic acid (0.693 g, 27%) as a foam.

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue dissolved in ethyl ether (20 ml)
  3. washThe solution was washed with 1N HCl solution and brine
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent was evaporated
  6. customthe crude was purified by flash chromatography
  7. additiona mixture of EA/H (1/3) as eluent

Sources & evidence

ORD record
ord-4a6238a676b54927aebafa69272d91a4
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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