Trifluoroacetic acid → HCID 86758043, compound

HRID 1934404Notes

Reaction equation

HRID 1934404 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:18][CH:17]([CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([NH:31][C@H:32]([C:37]#[CH:38])[CH2:33][C:34]([OH:36])=[O:35])=[O:30])[CH2:24]2)=[O:22])[CH2:16]1)=O)(C)(C)C>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:15]1[CH2:18][CH:17]([CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([NH:31][C@H:32]([C:37]#[CH:38])[CH2:33][C:34]([OH:36])=[O:35])=[O:30])[CH2:24]2)=[O:22])[CH2:16]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86758045HCID 86758045, compound

Product 1

HCID 86758043HCID 86758043, compoundYield 23.6%

Procedure

Trifluoroacetic acid (3 ml) was added to N-[(R)-1-[3-(1-tert-butoxycarbonyl-3-azetidinyl)propanoyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine (1.11 g, 2.55 mmol). The reaction mixture was stirred for 1 hour at room temperature. Solvent was evaporated in vacuo. The residue was purified by HPLC to give N-[(R)-1-[3-(3-azetidinyl)propanoyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine trifluoroacetate (270 mg, 23.6%).

Workup

  1. customSolvent was evaporated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-876633ded9cc4b6194e35b7eb75b0cfe
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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