Sodium Hydroxide → HCID 66688142, compound

HRID 1971862Notes

Reaction equation

HRID 1971862 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@@H:14]([C:22]([OH:24])=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O:32]1[CH2:37][CH2:36][CH:35]([CH2:38][N:39]2[CH2:44][CH2:43][CH:42]([CH2:45][NH2:46])[CH2:41][CH2:40]2)[CH2:34][CH2:33]1.[OH-].[Na+]>ClCCl>[C:28]([O:27][C:25](=[O:26])[NH:13][C@@H:14]([C:22](=[O:24])[NH:46][CH2:45][CH:42]1[CH2:41][CH2:40][N:39]([CH2:38][CH:35]2[CH2:34][CH2:33][O:32][CH2:37][CH2:36]2)[CH2:44][CH2:43]1)[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 637610Boc-D-phenylalanineHCID 22313260HCID 22313260, compound

Product 1

HCID 66688142HCID 66688142, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6.7 g of carbonyldiimidazole is added to a solution of 10 g of Boc-D-Phe-OH in 80 ml of dichloromethane, cooled to 0° C. The resulting solution is maintained under stirring at 0° C. for 1 hour. A solution consisting of 8.0 g of (11) in 20 ml of dichloromethane is then dripped into the reaction mixture at a rate such that the temperature does not exceed 5° C. The solution is maintained under stirring at 0° C. for 1 hour, and at ambient temperature for 2 hours. 100 ml of 1M NaOH is added to the mixture, the two phases are separated, the organic phase is washed with water (2×), and after a low-pressure solvent change with ethyl acetate, compound (12) is crystallised from ethyl acetate to obtain 14.64 g of white solid. Yield 85%.

Workup

  1. temperatureThe resulting solution is maintained
  2. customdoes not exceed 5° C
  3. temperatureThe solution is maintained
  4. stirringunder stirring at 0° C. for 1 hour
  5. waitat ambient temperature for 2 hours
  6. customthe two phases are separated
  7. washthe organic phase is washed with water (2×)
  8. customafter a low-pressure solvent change with ethyl acetate, compound (12) is crystallised from ethyl acetate

Sources & evidence

ORD record
ord-bcc31fdfc5ab417cb9d61a0c699b6734
Source dataset
uspto-grants-2013_04
Patent number
US08431684B2

Reaction notes

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