p-Toluenesulfonic acid → HCID 131720843, compound

HRID 2395173Notes

Reaction equation

HRID 2395173 reaction equation
CN1CCOCC1.[NH:8]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:9]([C:18]([OH:20])=O)[CH2:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].O.[NH2:32][C@H:33]([C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[CH:34]([CH3:36])[CH3:35].S(O)(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[NH:8]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:9]([C:18]([NH:32][C@H:33]([C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[CH:34]([CH3:36])[CH3:35])=[O:20])[CH2:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 79724-MethylmorpholineHCID 6950584benzyl (2S)-2-amino-3-methylbutanoateHCID 74892349Z-Asp(OtBu)-OH·H2O

Product 1

HCID 131720843HCID 131720843, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.83 g of 1-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate and 9 ml of N-methylmorpholine were added to a solution of 13.65 g of Z-Asp(OBut)-OH.H2O and 15.9 g of Val-OBzl.TosOH in 250 ml of DMF. After stirring for 2 hours the reaction mixture was evaporated in a vacuum and the residue was partitioned between ethyl acetate and water. The organic phase was washed with 5% KHSO4 /10% K2SO4 solution, water, saturated NaHCO3 solution, water and saturated NaCl solution, dried over Na2SO4, filtered and evaporated. The residue was crystallized from diethyl ether/hexane and there were obtained 17.5 g of Z-Asp(OBut)-Val-OBzl of m.p. 99°; [a]D20 -27.7° (c=1, MeOH).

Workup

  1. customwas evaporated in a vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with 5% KHSO4 /10% K2SO4 solution, water, saturated NaHCO3 solution, water and saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-b1afa26a1502437d88bba49d034f5812
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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