Hydrochloric Acid → HCID 68455930, compound

HRID 2356842Notes

Reaction equation

HRID 2356842 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:20]2[CH:24]=[C:23]([NH2:25])[N:22]([C:26]([CH3:29])([CH3:28])[CH3:27])[N:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]([NH:40][C@H:41]([C:43](O)=[O:44])[CH3:42])([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].O=P(Cl)(Cl)Cl.Cl>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:20]2[CH:24]=[C:23]([NH:25][C:43](=[O:44])[CH:41]([NH:40][C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH3:42])[N:22]([C:26]([CH3:29])([CH3:28])[CH3:27])[N:21]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 736104N-carbobenzyloxyalanineHCID 59385407HCID 59385407, compound

Product 1

HCID 68455930HCID 68455930, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.68 g (1.7 mmol) of 4-(5-amino-1-tert-butyl-1H-pyrazol-3-yl)-4-phenylpiperidine-1-carboxylic acid tert-butyl ester and 0.39 g (1.7 mmol) of carbobenzyloxy-L-alanine in 9.0 mL of dry pyridine was stirred at −10° C. as 0.18 mL (1.9 mmol) of POCl3 was added. After 25 min, the reaction mixture was poured into 1M HCl and extracted with EtOAc. The organic layer washed with sat. aq. NaHCO3, dried over MgSO4 and concentrated. Purification on silica gel using 50:50 EtOAc-hexanes as eluant afforded 4-[5-(2-benzyloxycarbonylamino-propionylamino)-1-tert-butyl-1H-pyrazol-3-yl]-4-phenylpiperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. additionwas added
  2. extractionextracted with EtOAc
  3. washThe organic layer washed with sat. aq. NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification on silica gel using 50:50 EtOAc-hexanes as eluant

Sources & evidence

ORD record
ord-f17f5344aaf74060aa689193832cfd68
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

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