Ammonium Chloride → HCID 86588566, compound

HRID 1368888Notes

Reaction equation

HRID 1368888 reaction equation
O=[C:2]([CH2:8][CH3:9])[CH2:3][CH2:4][C:5]([OH:7])=O.C(Cl)(=[O:15])C(C)(C)C.[NH2:17][CH:18]([P:22]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)([O:24][C@@H:25]([CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:23])[CH:19]([CH3:21])[CH3:20].[Cl-].[NH4+]>C(Cl)Cl.C(N(CC)CC)C>[CH2:44]([O:43][C:41]([NH:40][CH2:39][CH2:38][CH2:37][CH2:36][C@H:25]([O:24][P:22]([CH:18]([NH:17][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:8](=[O:15])[CH3:9])[CH:19]([CH3:21])[CH3:20])([O:51][CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[O:23])[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:42])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 37997744-Oxohexanoic acidHCID 86588567HCID 86588567, compound

Product 1

HCID 86588566HCID 86588566, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-Oxohexanoic acid (56.2 μl) was dissolved in methylene chloride (1.4 ml), and the solution was added with triethylamine (98.5 μl) and pivalic chloride (58.0 μl) and stirred under an argon atmosphere at room temperature for 15 minutes. The resulting mixture was added to a methylene chloride (1.4 ml) solution of the crude benzyl (S)-2-((1-amino-2-methylpropyl)(benzyloxyphosphinoyl)oxy)-6-benzyloxycarbonylaminohexanate (140.5 mg) obtained in the step (e) of Example 24, and the mixture was further stirred at room temperature for 4 hours. Saturated aqueous ammonium chloride was added to the mixture, and then the organic substances were extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15 g, hexane:acetone=3:1) to obtain benzyl (S)-6-benzyloxycarbonylamino-2-((2-methyl-1-(5-oxohexanoylamino)propyl)(benzyloxyphosphinoyl)oxy)hexanoate (105.4 mg, 63.1%). This compound was subjected to the measurement of molecular weight and then used in the following reaction without further purification.

Workup

  1. customobtained in the step (e) of Example 24
  2. stirringthe mixture was further stirred at room temperature for 4 hours
  3. extractionthe organic substances were extracted with ethyl acetate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (15 g, hexane:acetone=3:1)

Sources & evidence

ORD record
ord-84fd4438ced14b6b9bb13c6a5122da47
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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