Acetone → HCID 131734639, compound

HRID 2207003Notes

Reaction equation

HRID 2207003 reaction equation
[CH2:1]([NH2:5])[C:2]([OH:4])=[O:3].C[C:7]([CH3:9])=[O:8].[NH:10]([C:33]([CH3:35])=[O:34])[C@H:11]([C:23](ON1C(=O)CCC1=O)=[O:24])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([CH3:22])=[O:21])=[CH:15][CH:14]=1>C(=O)(O)[O-].[Na+]>[NH:10]([C:33]([CH3:35])=[O:34])[C@H:11]([C:23]([NH:5][CH2:1][C:2]([O:4][N:10]1[C:33](=[O:34])[CH2:35][CH2:9][C:7]1=[O:8])=[O:3])=[O:24])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([CH3:22])=[O:21])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 750GlycineHCID 131734640HCID 131734640, compound

Product 1

HCID 131734639HCID 131734639, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

11 g of L-glycine was dissolved in 300 ml of 10% sodium bicarbonate. 150 ml of acetone and 36 g of Ac-Tyr(Ac)-OSu were added into the reaction mixture. The mixture was stirred for 5 h at RT. The mixture was washed with ether (1×300 ml). 500 ml of ethyl acetate was added into the aqueous layer. The pH of the mixture was adjusted to 2.4-2.5 with ice-cooled 3 N HCl. The ethyl acetate layer was collected and washed with water (3×300 ml). The organic solution was dried over sodium sulfate. The solution was evaporated to dryness. 28 g of the residue (Ac-Tyr(Ac)-Gly-OH) and 13 g of N-hydroxysuccinimide were dissolved in 300 ml of dichloromethylene. The mixture was cooled to 0° C. 18 g of 1,3-dicyclohexylcarbodiimide was added into the reaction mixture. The mixture was stirred for 1 hour at 0° C. The solid was removed by filtration. The dichloromethylene solution was washed with 5% sodium bicarbonate (1×200 ml) and water (3×200 ml). The organic solution was dried over sodium sulfate. The solution was evaporated to dryness to yield 20 g Ac-Tyr(Ac)-Gly-OSu.

Workup

  1. washThe mixture was washed with ether (1×300 ml)
  2. addition500 ml of ethyl acetate was added into the aqueous layer
  3. temperaturecooled 3 N HCl
  4. customThe ethyl acetate layer was collected
  5. washwashed with water (3×300 ml)
  6. dry with materialThe organic solution was dried over sodium sulfate
  7. customThe solution was evaporated to dryness
  8. dissolution28 g of the residue (Ac-Tyr(Ac)-Gly-OH) and 13 g of N-hydroxysuccinimide were dissolved in 300 ml of dichloromethylene
  9. temperatureThe mixture was cooled to 0° C
  10. addition18 g of 1,3-dicyclohexylcarbodiimide was added into the reaction mixture
  11. stirringThe mixture was stirred for 1 hour at 0° C
  12. customThe solid was removed by filtration
  13. washThe dichloromethylene solution was washed with 5% sodium bicarbonate (1×200 ml) and water (3×200 ml)
  14. dry with materialThe organic solution was dried over sodium sulfate
  15. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-5d58eaf0d27c426f8423f032526eea34
Source dataset
uspto-grants-2016_06
Patent number
US09376381B2

Reaction notes

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