p-Toluenesulfonate → HCID 178512181, compound

HRID 246923Notes

Reaction equation

HRID 246923 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH2:12]([O:19][C:20](=[O:23])[CH2:21][NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:24]([C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[C@H:25]([C:36](O)=[O:37])[CH2:26][CH2:27][CH2:28][NH:29][C:30](=[NH:35])[NH:31][N+:32]([O-:34])=[O:33].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[NH:24]([C:39]([O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40])[C@H:25]([C:36]([NH:22][CH2:21][C:20]([O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:23])=[O:37])[CH2:26][CH2:27][CH2:28][NH:29][C:30](=[NH:35])[NH:31][N+:32]([O-:34])=[O:33]

Participants

7

Reactant 4

HCID 85570p-ToluenesulfonateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 409140Benzyl glycinateHCID 178512185HCID 178512185, compound

Product 1

HCID 178512181HCID 178512181, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

353 g of tosylate of glycine benzyl ester (H-Gly-o-Bzl, Tosylate) are dissolved in 2 liters of DMF; 115 g of NEM then 353 g of Z-Arg(NO2)-OH and finally 500 g of BOP are added. The pH of the medium is adjusted to 7 with the aid of NEM and using pH indicating paper on samples of the reaction medium diluted with water. The reaction medium is stirred and the state of advance of the reaction followed by TLC. After 4 hrs., the reaction is complete and the medium evaporated to dryness in vacuo at 35°. The residue of evaporation is taken up in 2 liters of ethyl acetate and 2 liters of water. Under these conditions, a solid is obtained which is drained and washed successively in solid phase with a 5% aqueous solution of HKSO4 +K2SO4, with pure water, with a 5% aqueous solution of NaHCO3 and finally water.

Workup

  1. customon samples of the reaction
  2. customthe medium evaporated to dryness in vacuo at 35°
  3. customThe residue of evaporation
  4. customUnder these conditions, a solid is obtained which
  5. washwashed successively in solid phase with a 5% aqueous solution of HKSO4 +K2SO4, with pure water, with a 5% aqueous solution of NaHCO3 and finally water

Sources & evidence

ORD record
ord-71afb12c9b584f79930e5f4534985a72
Source dataset
uspto-grants-1987_11
Patent number
US04704450

Reaction notes

Loading…