p-Toluenesulfonic acid → HCID 131724632, compound

HRID 1824578Notes

Reaction equation

HRID 1824578 reaction equation
N(C(OC(C)(C)C)=O)CC(NCC(NCC(N[C@H](C(O)=O)CC1C=CC=CC=1)=O)=O)=O.ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC(=O)CCCCN)C1C=CC=CC=1.[NH:81]([C:119]([O:121][C:122]([CH3:125])([CH3:124])[CH3:123])=[O:120])[CH2:82][C:83]([NH:85][CH2:86][C:87]([NH:89][CH2:90][C:91]([NH:93][C@H:94]([C:102]([NH:104][CH2:105][CH2:106][CH2:107][CH2:108][C:109]([O:111]CC1C=CC=CC=1)=[O:110])=[O:103])[CH2:95][C:96]1[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=1)=[O:92])=[O:88])=[O:84]>CN(C=O)C.CO.O.[Pd].C(N(CC)CC)C>[NH:81]([C:119]([O:121][C:122]([CH3:125])([CH3:124])[CH3:123])=[O:120])[CH2:82][C:83]([NH:85][CH2:86][C:87]([NH:89][CH2:90][C:91]([NH:93][C@H:94]([C:102]([NH:104][CH2:105][CH2:106][CH2:107][CH2:108][C:109]([OH:111])=[O:110])=[O:103])[CH2:95][C:96]1[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=1)=[O:92])=[O:88])=[O:84]

Participants

12

Reactant 6

HCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 7019821benzyl 5-aminovalerateHCID 131724633HCID 131724633, compoundHCID 131725735HCID 131725735, compound

Product 1

HCID 131724632HCID 131724632, compound

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

Boc-Gly-Gly-Gly-Phe-OH (575 mg) (SEQ ID NO. 8), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the mixture was stirred for 30 minutes. The solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred for 3 days at room temperature. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO. 8). The Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (SEQ ID NO. 8) (380 mg) was dissolved in methanol containing 50% of water (20 ml), and the solution was added with 5% Pd—C (water content; 50%, 300 mg) and stirred overnight under hydrogen at ordinary pressure. The catalyst in the reaction mixture was removed by filtration, and the filtrate was concentrated to dryness to obtain Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOH (SEQ ID NO. 8) (330 mg).

Workup

  1. stirringthe mixture was stirred for 3 days at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography (CH2Cl2:MeOH=20:1)
  4. customto obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO
  5. stirringstirred overnight under hydrogen at ordinary pressure
  6. customThe catalyst in the reaction mixture was removed by filtration
  7. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-4cf601c6e85a453694d4fe40ef680bde
Source dataset
uspto-grants-2006_05
Patent number
US07041818B2

Reaction notes

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