Glycine methyl ester → Z-Trp-Gly-OCH3

HRID 2295711Notes

Reaction equation

HRID 2295711 reaction equation
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].C(=O)(O)[O-].[Na+].CP(OP(CC)(C)=O)(CC)=O>CN(C)C=O.O>[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@H:2]([C:13]([NH:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

7

Reactant 4

HCID 69221Glycine methyl esterHCID 101176benzyloxycarbonyl-L-tryptophanHCID 103894Phosphinic acid, P-ethyl-P-methyl-, P,P'-anhydrideHCID 516892Sodium Bicarbonate2×

Product 1

HCID 1823118Z-Trp-Gly-OCH3

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To the suspension of 3.35 g (0.01 mol) of Z-Trp-OH and 1.25 g (0.01 mol) of H-Gly-OCH3 in 15 ml of dimethyl formamide there were added portionwise altogether 7 ml of water and subsequently 5.1 g of a finely powdered sodium bicarbonate. The suspension was largely clarified by adding dropwise 4 ml of methylethyl phosphinic acid anhydride. A sample of the reaction solution diluted with water showed a neutral reaction. Upon heating to room temperature the solution was stirred overnight and the solvents were separated by distillation in a high vacuum at room temperature. The residue was taken up in a mixture of 25 ml of water and 70 ml of ethyl acetate, the ethyl acetate extract was separated and the aqueous phase was extracted twice using each time 10 ml of ethyl acetate. The combined ethyl acetate extracts were washed twice using each time 7 ml of water, a 5% potassium bisulfate solution (until an acid reaction took place) and a saturated sodium bicarbonate solution (until s slightly alkaline reaction took place). Upon drying over magnesium sulfate the ethyl acetate solution was largely separated by distillation in vacuo and the residue was digested with diisopropyl ether.

Workup

  1. customa neutral reaction
  2. customthe solvents were separated by distillation in a high vacuum at room temperature
  3. additionThe residue was taken up in a mixture of 25 ml of water and 70 ml of ethyl acetate
  4. extractionthe ethyl acetate extract
  5. customwas separated
  6. extractionthe aqueous phase was extracted twice
  7. washThe combined ethyl acetate extracts were washed twice
  8. customa 5% potassium bisulfate solution (until an acid reaction
  9. customuntil s slightly alkaline reaction
  10. dry with materialUpon drying over magnesium sulfate the ethyl acetate solution
  11. customwas largely separated by distillation in vacuo

Sources & evidence

ORD record
ord-f22d599f36a6497393690f178f7b620b
Source dataset
uspto-grants-1984_01
Patent number
US04426325

Reaction notes

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