Sodium Hydroxide → HCID 76413410, compound

HRID 3709Notes

Reaction equation

HRID 3709 reaction equation
[C:1]1([C:24]([NH:26][C@H:27]([C:30]([OH:32])=[O:31])[CH2:28][OH:29])=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([NH:17][C@H:18]([C:21]([OH:23])=[O:22])[CH2:19][OH:20])=[O:16].[OH-].[Na+]>CO>[C:1]([O:20][CH2:19][CH:18]([NH:17][C:15](=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:8][S:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:24](=[O:25])[NH:26][CH:27]([C:30]([OH:32])=[O:31])[CH2:28][O:29][C:10]([CH3:15])([CH3:11])[CH3:9])[C:21]([OH:23])=[O:22])([CH3:24])([CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 468888HCID 468888, compound

Product 1

HCID 76413410HCID 76413410, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N,N'-[dithiobis(2,1-phenylene carbonyl)]bis L-serine bis[O(1,1-dimethylethyl) bis (1,1-dimethylethyl)ester (1.0 g, 1.4 mmol) from Example 39, in 30 mL methanol was treated with 8 mL of 1N NaOH and allowed to stir for 18 hours. The methanol was removed in vacuo and the residual was diluted with 5 water and extracted with ethyl acetate. A slow stream of oxygen was passed thru the aqueous layer while dilute HCl was added to maintain a pH=6-7. After the disulfide formation was complete (2-18 hours), dilute HCL was added to a pH=3. The product was collected by filtration, washed with water, dried and was recrystallized from ethyl acetate to afford 0.4 g of the title compound, mp 206°-207° C.

Workup

  1. customThe methanol was removed in vacuo
  2. additionthe residual was diluted with 5 water
  3. extractionextracted with ethyl acetate
  4. additionwas added
  5. temperatureto maintain a pH=6-7
  6. custom(2-18 hours)
  7. additiondilute HCL
  8. additionwas added to a pH=3
  9. filtrationThe product was collected by filtration
  10. washwashed with water
  11. customdried
  12. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a67bdc641f8e4f39ae974ec2f00e4563
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Reaction notes

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