Water → HCID 86594403, compound

HRID 895352Notes

Reaction equation

HRID 895352 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C@@H:6]([C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[NH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[CH2:20][CH2:19][CH2:18][NH:17][C:16]=2[N:15]=1)[CH3:2].C1C=CC(O[C:40](OC2C=CC=CC=2)=[N:41][C:42]#[N:43])=CC=1.O.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C@@H:6]([C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[CH2:20][CH2:19][CH2:18][NH:17][C:16]=3[N:15]=2)[C:40]1=[N:41][C:42]#[N:43])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 688090Diphenyl N-CyanocarbonimidateHCID 11123088HCID 11123088, compound

Product 1

HCID 86594403HCID 86594403, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A solution of the diamine 1-2 (120 mg, 0.27 mmol), diphenyl cyanocarbonimidate (65 mg, 0.27 mmol) and K2C03 (94 mg, 0.68 mmol) in EtOAc (10 mL) and water (5 mL) was stirred at room temperature for 16 hours then heated to 75° C. for 6 hours. After cooling, the mixture was poured into saturated Na2CO3, extracted with EtOAc and washed successively with water and brine. The EtOAc layer was dried (MgSO4) and concentrated in vacuo to give 1-3 an oil which was used as such in the next step.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. washwashed successively with water and brine
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give 1-3 an oil which

Sources & evidence

ORD record
ord-06eaac12e35447e6b3be6642e647d5fd
Source dataset
uspto-grants-2005_07
Patent number
US06916810B2

Reaction notes

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