Acetic Acid → HCID 86736052, compound

HRID 1111629Notes

Reaction equation

HRID 1111629 reaction equation
CC(C)([O-])C.[K+].[N+:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[C-:8].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:25]=[C:24](OP(N3CCOCC3)(N3CCOCC3)=O)[CH2:23][N:22]=[C:21]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[F:47])[C:20]=2[CH:48]=1.C(O)(=O)C>O1CCCC1.O>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:25]3[CH:8]=[N:7][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:24]3[CH2:23][N:22]=[C:21]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[F:47])[C:20]=2[CH:48]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 533707Ethyl isocyanoacetateHCID 12441372HCID 12441372, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 86736052HCID 86736052, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide, 1.4 g (0.0125 mole), was added to a solution of 1.4 g (0.0124 mole) of ethyl isocyanoacetate in 125 ml of dry tetrahydrofuran. After stirring under argon for 10 minutes, 5.07 g (0.01 mole) of 7-chloro-2-[bis(morpholino)-phosphinyloxy]-5-(2-fluorophenyl)-3H-1,4-benzodiazepine was added and stirring was continued for 30 minutes at room temperature. The reaction mixture was then acidified with glacial acetic acid, diluted with water and extracted with methylene chloride. The extracts were washed with saturated sodium bicarbonate solution, dried and evaporated. Crystallization of the residue from ether yielded crystals which were recrystallized from methylene chloride/ether/hexane for analysis, mp 195°-196°.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes at room temperature
  3. extractionextracted with methylene chloride
  4. washThe extracts were washed with saturated sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. customCrystallization of the residue from ether yielded crystals which
  8. customwere recrystallized from methylene chloride/ether/hexane for analysis, mp 195°-196°

Sources & evidence

ORD record
ord-25ac7fb488c44e43a7c3ee4728a4033d
Source dataset
uspto-grants-1978_10
Patent number
US04118386

Reaction notes

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