p-Toluenesulfonic acid → HCID 131718825, compound

HRID 1768872Notes

Reaction equation

HRID 1768872 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[NH:19][C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:12]=1)=[O:7])([CH3:4])[CH3:3].[NH2:23][C@H:24]([C:29]([OH:31])=O)[CH2:25][CH:26]([CH3:28])[CH3:27].N[C@H](C([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=O)CC1C=CC=CC=1.CC1C=CC(S(O)(=O)=[O:59])=CC=1.C(=O)(O)[O-].[Na+].C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>O1CCCC1>[CH3:4][C:2]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[NH:19][C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:12]=1)=[O:7])([CH3:1])[CH3:3].[NH2:23][C@H:24]([C:29]([NH:19][C@H:11]([C:10]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:59])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:31])[CH2:25][CH:26]([CH3:27])[CH3:28]

Participants

8

Reactant 6

HCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 516892Sodium BicarbonateHCID 736312Benzyl 3-phenyl-L-alaninateHCID 131718826HCID 131718826, compound

Product 1

HCID 131718825HCID 131718825, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Condensation of Boc-trp-Leu-OH (part B of example of above-cited U.S. Pat. No. 4,472,305, 14.0 g.) and H-Phe-OBzl (freed from 14.33 g. of the p-toluenesulfonate salt with sodium bicarbonate) using dicyclohexylcarbodiimide (6.91 g.) and N-hydroxysuccinimide (3.86 g.) in tetrahydrofuran (250 ml.) at 0° C. for 1 hr. and then at room temperature overnight, isolation by ethyl acetate extraction, and purification by crystallization from methanol-ether-hexane gave Boc-trp-Leu-Phe-OBzl (16.9 g., 77% yield, m.r. 140°-142° C.).

Workup

  1. customat 0° C.
  2. customfor 1 hr
  3. extractionand then at room temperature overnight, isolation by ethyl acetate extraction, and purification
  4. customby crystallization from methanol-ether-hexane

Sources & evidence

ORD record
ord-ee8e4b4940a54b5a8e668fafa9ef456e
Source dataset
uspto-grants-1995_01
Patent number
US05378803

Reaction notes

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