Acetic Acid → HCID 131732133, compound

HRID 1399500Notes

Reaction equation

HRID 1399500 reaction equation
[Br:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[NH2:7][CH2:8][CH2:9][S:10][C:11]([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.CCN(C(C)C)C(C)C.CC(O)=O>C(Cl)Cl>[Br:1][CH2:2][CH2:3][C:4]([NH:7][CH2:8][CH2:9][S:10][C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 84944Propanoyl chloride, 3-bromo-HCID 262764S-Tritylcysteamine

Product 1

HCID 131732133HCID 131732133, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromopropionylchloride (62.5 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), 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 Br—(CH2)2CONH—(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-66f0cae97097448985d6c23b79b91884
Source dataset
uspto-grants-2014_12
Patent number
US08906847B2

Reaction notes

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