1-Hydroxybenzotriazole → HCID 131731158, compound

HRID 926426Notes

Reaction equation

HRID 926426 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:4]([NH:6][CH2:7][C:8]([OH:10])=O)=[O:5])C.[NH2:28][C@H:29]([CH:37]=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[CH3:39]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.ClCCl>[NH2:28][C@H:29]([C:37]([NH:1][CH2:2][C:4]([NH:6][C@H:7]([CH:8]=[O:10])[CH3:39])=[O:5])=[O:38])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 446207HCID 446207, compoundHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7019065HCID 7019065, compound2×

Product 1

HCID 131731158HCID 131731158, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(Phe)-H was synthesized by the solid phase reaction method using CTC as a solid phase carrier. Furthermore, similar to Example 7, Fmoc-Ala-Gly-OH was synthesized. Then, to dichloromethane (2 ml) were added CTC-Phe-H (110 mg (0.145 mmol)), Fmoc-Ala-Gly-OH (160 mg (0.4 mmol)), HBTU (165 mg (0.4 mmol)), HOBt (60 mg (0.4 mmol)), dimethylformamide (1 ml) and diisopropylethylamine (75 μl (0.4 mmol)), respectively, and the mixture was stirred to react at room temperature for 2 hours. After the reaction, the solid phase was washed with dimethylformamide (3×2 ml), methanol (3×2 ml) and dichloromethane (3×2 ml), respectively. Subsequently, to the above solid phase was added the previously prepared Fmoc deprotection solution (dimethylformamide:piperidine:DBU=96:2:2) (2 ml), and the mixture was stirred to react at room temperature for 1 hour to obtain CTC-Phe-Gly-Ala-H.

Workup

  1. customto react at room temperature for 2 hours
  2. customAfter the reaction
  3. washthe solid phase was washed with dimethylformamide (3×2 ml), methanol (3×2 ml) and dichloromethane (3×2 ml)
  4. additionSubsequently, to the above solid phase was added the previously prepared Fmoc deprotection solution (dimethylformamide:piperidine:DBU=96:2:2) (2 ml)
  5. stirringthe mixture was stirred
  6. customto react at room temperature for 1 hour

Sources & evidence

ORD record
ord-82be9c9f477243a2a46c93dbe4aed6bd
Source dataset
uspto-grants-2016_03
Patent number
US09284348B2

Reaction notes

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