Acetic Acid → Acetamide, 2-bromo-N-[2-[(triphenylmethyl)thio]ethyl]-

HRID 1399502Notes

Reaction equation

HRID 1399502 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH2:6][CH2:7][CH2:8][S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C.CC(O)=O>C(Cl)Cl>[Br:1][CH2:2][C:3]([NH:6][CH2:7][CH2:8][S:9][C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 262764S-Tritylcysteamine

Product 1

HCID 11259232Acetamide, 2-bromo-N-[2-[(triphenylmethyl)thio]ethyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromoacetylbromide (54 μl, 0.62 mmol) was dissolved in 0.5 ml CH2Cl2 and added to a solution of H2N—CH2—CH2-STrt (200 mg, 0.56 mmol) and DIEA (196 μl, 1.1 mmol) in CH2Cl2 (1 ml). The mixture was stirred for 1 h at RT. The reaction mixture was acidified with AcOH (100 μl) and the solvent was removed in vacuo. The residue was purified over silica gel (heptane/EtOAc=1:1) to obtain product Br—CH2—CONH—(CH2)2-STrt.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified over silica gel (heptane/EtOAc=1:1)

Sources & evidence

ORD record
ord-ac292778c3bc4968a656a869010639cf
Source dataset
uspto-grants-2014_12
Patent number
US08906847B2

Reaction notes

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