Hydrochloric Acid → HCID 131728986, compound

HRID 2428201Notes

Reaction equation

HRID 2428201 reaction equation
C[O:2][C:3]([C@@H:5]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[O:23][N:22]=[C:21]([C:24]4[C:29]([F:30])=[CH:28][CH:27]=[C:26]([F:31])[C:25]=4[Cl:32])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:6]1)=[O:4].[OH-].[Na+].Cl>C1COCC1>[C:36]([O:35][C:33]([N:7]1[CH2:8][CH2:9][C@H:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3[O:23][N:22]=[C:21]([C:24]4[C:29]([F:30])=[CH:28][CH:27]=[C:26]([F:31])[C:25]=4[Cl:32])[CH:20]=3)=[CH:15][CH:16]=2)[C@@H:5]([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131728987HCID 131728987, compound

Product 1

HCID 131728986HCID 131728986, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A sol. of compound D1 (2.00 g, 3.72 mmol) in THF (30 mL) and aq. 1M NaOH (30 mL) was stirred at 70° C. overnight. Aq. 1M HCl was added until a pH=4 was reached. The mixture was extracted with EtOAc (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying under high vacuum yielded the crude title compound (2.04 g, quantitative yield) that was used further without purification. LC-MS: tR=1.08 min; ES+: 549.31.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customDrying under high vacuum

Sources & evidence

ORD record
ord-52e2aa722a7242fdb8563d8cf3621fbd
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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