Chloroform methanol → HCID 178427543, compound

HRID 723009Notes

Reaction equation

HRID 723009 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:41][CH2:40][CH2:39][C@H:28]1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:24])[NH:13][S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:5])[CH3:3].C(Cl)(Cl)[Cl:50].CO>Cl.C(OCC)(=O)C>[NH:1]([Cl:50])[C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:41][CH2:40][CH2:39][C@H:28]1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:24])[NH:13][S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:5])[CH3:3]

Participants

5

Reactant 2

HCID 21584188Chloroform methanolHCID 178427549HCID 178427549, compound2×

Product 1

HCID 178427543HCID 178427543, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 137 mg (0.2 mmol) of Boc-Ala-Arg(Tos)-Pro-OBzl in 3 ml of hydrogen chloride in ethyl acetate (4 mol/L) was stirred at room temperature for 2 h and TLC (chloroform/methanol, 20:1) indicated complete disappearance of Boc-Ala-Arg(Tos)-Pro-OBzl. The reaction mixture was evaporated under reduced pressure with ethyl acetate, repeatedly, to remove hydrogen chloride. The residue was triturated with ether to provide the title compound as a colorless powder, which was used for the next reaction directly.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure with ethyl acetate
  2. customrepeatedly, to remove hydrogen chloride
  3. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-b9cb7760af0c4519b5ffe30a9cda91c9
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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