Trityl chloride → HCID 14217168, compound

HRID 989573Notes

Reaction equation

HRID 989573 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]([NH:12][C:13]([CH2:15][NH2:16])=[O:14])[C:9]([OH:11])=[O:10])=[CH:5][CH:6]=1.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.CC(O)C.C(NCC)C>[NH:16]([C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:15][C:13]([NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:14]

Participants

6

Reactant 2

HCID 6456Trityl chlorideHCID 929533321-03-7

Product 1

HCID 14217168HCID 14217168, compoundYield 64.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3776IsopropanolSolventHCID 8021DiethylamineSolvent

Procedure

Production of compound (22) was conducted in substantially the same manner as in step 1 of Example 6. That is, Gly-Phe (manufactured and sold by PEPTIDE INSTITUTE INC., Japan, 1.1 g, 5 mmol) was dissolved in a mixture of 2 ml of H2O, 2 ml of 2-propanol and 1.5 ml of diethylamine, to obtain a solution. To the obtained solution was portionwise added trityl chloride (1.8 g, 6.5 mmol), followed by stirring for one hour. To the resultant reaction mixture was added H2O, to thereby generate a precipitate. The generated precipitate was collected, washed with water and then dissolved into 5 ml of acetic acid, to thereby obtain an acidic solution. The obtained acidic solution was evaporated to dryness under reduced pressure, to thereby obtain 1.5 g of Trt-Gly-Phe.

Workup

  1. customto obtain a solution
  2. customTo the resultant reaction mixture
  3. customThe generated precipitate was collected
  4. washwashed with water
  5. dissolutiondissolved into 5 ml of acetic acid
  6. customto thereby obtain an acidic solution
  7. customThe obtained acidic solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e480b9e94db542f2a0a4bff3d0d74ba9
Source dataset
uspto-grants-2002_10
Patent number
US06458347B1

Reaction notes

Loading…