HCID 22660808, compound → Trifluoroacetic acid

HRID 392970Notes

Reaction equation

HRID 392970 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]4[N:17]=[N:18][NH:19][N:20]=4)=[CH:15][C:10]=3[N:9]=[C:8]2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[N:33]=[C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH3:41])[O:31][N:30]=3)=[CH:23][CH:22]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)Cl.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46].C([SiH](C(C)C)C(C)C)(C)C>>[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]4[NH:17][N:18]=[N:19][N:20]=4)=[CH:15][C:10]=3[N:9]=[C:8]2[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]3[N:33]=[C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH3:41])[O:31][N:30]=3)=[CH:25][CH:26]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46]

Participants

4

Reactant 2

HCID 22660808HCID 22660808, compoundHCID 131724618HCID 131724618, compound

Product 2

HCID 6422Trifluoroacetic acidYield 70%HCID 178489361HCID 178489361, compound

Procedure

Compound 37 from the preceding experiment was added to 2.0 mL of methylene chloride:TFA:triisopropylsilane (6:2:0.5). The mixture was shaken at rt for 20 min and was filtered. The resin was washed with methylene chloride (2×2 mL). The washings and filtrate were combined and concentrated on a rotary evaporator to afford 34 as a TFA salt (56 mg, 70% yield). ESI MS m/e 549 (M+1). The product was identical to that described in Example 5.

Workup

  1. filtrationwas filtered
  2. washThe resin was washed with methylene chloride (2×2 mL)
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-59c13a7f07f14d6db3327e2691f1147e
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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