Hydrochloric Acid → HCID 15434915, compound

HRID 366478Notes

Reaction equation

HRID 366478 reaction equation
C(OC([N:8]([S:24]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)(=[O:26])=[O:25])[C@H:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]([O:12]C(C)(C)C)=[O:11])=O)(C)(C)C.Cl>C(Cl)Cl>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([N:30]2[CH2:29][CH2:28][N:27]([S:24]([NH:8][C@H:9]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:10]([OH:12])=[O:11])(=[O:26])=[O:25])[CH2:32][CH2:31]2)=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18727284HCID 18727284, compound

Product 1

HCID 15434915HCID 15434915, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-(R)-{tert-butoxycarbonyl-[4-(4-chlorophenyl)piperazine-1-sulfonyl]amino}-3-phenylpropionate (579 mg, 1.15 mmol), [prepared as described in Step 2 above], in methylene chloride (20 ml) was saturated with dry hydrogen chloride gas at 0° C. The reaction vessel was sealed and the reaction mixture was stirred at RT. After 72 h, the reaction mixture was vented with nitrogen and then concentrated in vacuo. The residue was treated with methylene chloride and the product was filtered to give 2-(R)-{[4-(4-chloro-phenyl)piperazine-1-sulfonyl]amino}-3-phenylpropionic acid as a white solid (74%), mp 176.0-178.0° C.

Workup

  1. customThe reaction vessel was sealed
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with methylene chloride
  4. filtrationthe product was filtered

Sources & evidence

ORD record
ord-6d1737421f0d46ab9bbf411ef55b3b89
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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