Sodium Hydroxide → HCID 66688142, compound

HRID 1971863Notes

Reaction equation

HRID 1971863 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+]>O1CCCC1>[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 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 tetrahydrofuran, 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 tetrahydrofuran is 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 1 hour. 100 ml of 1M NaOH is added to the mixture, and the tetrahydrofuran is evaporated at low pressure. Dichloromethane and water are added to the residue; 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 14.73 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 1 hour
  6. customthe tetrahydrofuran is evaporated at low pressure
  7. additionDichloromethane and water are added to the residue
  8. customthe two phases are separated
  9. washthe organic phase is washed with water (2×)
  10. customafter a low-pressure solvent change with ethyl acetate, compound (12) is crystallised from ethyl acetate

Sources & evidence

ORD record
ord-bf129c2526774217a53b35dc7b9697da
Source dataset
uspto-grants-2013_04
Patent number
US08431684B2

Reaction notes

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