Hydrochloric Acid → HCID 59278349, compound

HRID 559697Notes

Reaction equation

HRID 559697 reaction equation
[CH3:1][O:2][C:3](=[O:52])[C@@H:4]([NH:27][C:28](=[O:51])[CH:29]([NH:32][C:33]([C:35]1[C:36]2[CH:43]=[N:42][N:41]([C:44]3[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=3)[C:37]=2[CH:38]=[N:39][CH:40]=1)=[O:34])[CH2:30][CH3:31])[C@H:5]([O:7]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:6].Cl>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3](=[O:52])[C@@H:4]([NH:27][C:28](=[O:51])[CH:29]([NH:32][C:33]([C:35]1[C:36]2[CH:43]=[N:42][N:41]([C:44]3[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=3)[C:37]=2[CH:38]=[N:39][CH:40]=1)=[O:34])[CH2:30][CH3:31])[C@H:5]([OH:7])[CH3:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59278160HCID 59278160, compound

Product 1

HCID 59278349HCID 59278349, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a chilled (0° C.) solution of (2S,3R)-2-(2-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-butyrylamino)-3-trityloxy-butyric acid methyl ester (1.47 g, 2.10 mmol) in CH2Cl2 (100 mL) was added a 1 M solution of HCl (6.30 mL, 6.30 mmol) in ether. After 30 minutes, the reaction was quenched with saturated aqueous sodium bicarbonate (100 mL) and warmed to room temperature. After 30 minutes, the aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic layers were dried over MgSO4, filtered and passed through a pad of silica gel eluting with a gradient of 0-10% methanol in methylene chloride to afford (2S,3R)-2-(2-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-butyrylamino)-3-hydroxy-butyric acid methyl ester as white solid. MS m/z 458.76 (MH+).

Workup

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate (100 mL)
  2. waitAfter 30 minutes
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bc96307b0fbd4991b78d7ddf42fb475c
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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