Hydrochloric Acid → HCID 67527441, compound

HRID 2388642Notes

Reaction equation

HRID 2388642 reaction equation
C([O:5][C:6](=[O:45])[CH:7]([NH:21][C:22]1[C:27]([NH:28][CH2:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[CH:26][N:25]=[C:24]([N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])[N:23]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:20])[N:17]([CH3:19])[CH3:18])=[CH:11][CH:10]=1)(C)(C)C.[ClH:46]>C(O)=O>[ClH:46].[CH2:43]([N:40]([CH2:41][CH3:42])[C:24]1[N:23]=[C:22]([NH:21][CH:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:20])[N:17]([CH3:18])[CH3:19])=[CH:11][CH:10]=2)[C:6]([OH:45])=[O:5])[C:27]([NH:28][CH2:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)(=[O:31])=[O:32])=[CH:26][N:25]=1)[CH3:44]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67527972HCID 67527972, compound

Product 1

HCID 67527441HCID 67527441, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A formic acid (500 mL) solution of 2-{2-diethylamino-5-[(4-fluorobenzenesulfonyl)methylamino]-pyrimidin-4-ylamino}-3-(4-dimethylcarbamoyloxyphenyl) propionic acid t-butyl ester (28.69 g, 0.044 mol) was heated to 70° C. for 2 h, and then concentrated in vacuo. The residue was dissolved again in formic acid (500 mL), and then heated again at 70° C. for 2 h, and then concentrated again in vacuo. The residue was dissolved again in formic acid (500 mL), and then heated again at 70° C. for 1 h. The solution was reduced in volume by 90%, and then treated with 1.0 M HCl (44 mL, 0.044 mol) and distilled water (490 mL). The resulting homogeneous solution was concentrated in vacuo, and then distilled water (100 mL) was added, and the homogenous solution was lyophilized over 14 days to yield 26.76 g (96%) the title compound, as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved again in formic acid (500 mL)
  3. concentrationconcentrated again in vacuo
  4. dissolutionThe residue was dissolved again in formic acid (500 mL)
  5. temperatureheated again at 70° C. for 1 h
  6. distillationdistilled water (490 mL)
  7. concentrationThe resulting homogeneous solution was concentrated in vacuo
  8. additiondistilled water (100 mL) was added

Sources & evidence

ORD record
ord-1d46581c942745dab46829efbc1a0e8e
Source dataset
uspto-grants-2012_09
Patent number
US08269009B2

Reaction notes

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