Water → 2-(S-Triphenylmethylmercapto)ethylaminoacetyl-S-triphenylmethyl-L-cysteine ethyl ester

HRID 1417917Notes

Reaction equation

HRID 1417917 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C@H:5]([CH2:11][S:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:6][C:7](=[O:10])[CH2:8]Br)[CH3:2].C(N(CC)CC)C.[C:40]1([C:46]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[S:47][CH2:48][CH2:49][NH2:50])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.O>C(Cl)Cl.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:3][C:4](=[O:32])[C@H:5]([CH2:11][S:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:6][C:7](=[O:10])[CH2:8][NH:50][CH2:49][CH2:48][S:47][C:46]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 262764S-TritylcysteamineHCID 57318726N-Bromoacetyl-S-triphenylmethyl-L-cysteine ethyl ester

Product 1

HCID 702820382-(S-Triphenylmethylmercapto)ethylaminoacetyl-S-triphenylmethyl-L-cysteine ethyl esterYield 22%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of N-bromoacetyl-S-Triphenylmethyl-L-cysteine ethyl ester (1.0 g, 1.98 mmol.) and triethylamine (0.4 mL, 2.9 mmol.) in methylene chloride (10 mL) was added S-triphenylmethyl-2-aminoethanethiol (0.64 g, 2.0 mmol.). The reaction mixture allowed to stir at room temperature for seven days. Water (10 mL) was added. The organic layer was washed with NaHCO3 (2×10 mL), water (2×10 mL), and brine (10 mL), dried (magnesium sulfate), and concentrated in vacuo to give a foamy product. Flash chromatography using ethyl acetate:hexane (3:1) gave the product in 22% yield. MS (M+H)=751, calculated 751.3.

Workup

  1. washThe organic layer was washed with NaHCO3 (2×10 mL), water (2×10 mL), and brine (10 mL)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customto give a foamy product
  5. customgave the product in 22% yield

Sources & evidence

ORD record
ord-8a5ca501ad12497dad21c0735e22348d
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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