Trifluoroacetic acid → HCID 86590600, compound

HRID 1824425Notes

Reaction equation

HRID 1824425 reaction equation
C([O:3][CH:4]1[CH:8]([NH:9][C:10]([CH:12]2[N:16]3[C:17](=[O:36])[CH:18]([NH:23][C:24]([C:26]4[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH:29]=[CH:28][N:27]=4)=[O:25])[CH2:19][CH:20]=[CH:21][CH2:22][CH:15]3[CH2:14][CH2:13]2)=[O:11])[CH2:7][C:6](=[O:37])[O:5]1)C.FC(F)(F)C(O)=O>O>[OH:3][CH:4]1[CH:8]([NH:9][C:10]([C@H:12]2[N:16]3[C:17](=[O:36])[C@@H:18]([NH:23][C:24]([C:26]4[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH:29]=[CH:28][N:27]=4)=[O:25])[CH2:19][CH:20]=[CH:21][CH2:22][C@@H:15]3[CH2:14][CH2:13]2)=[O:11])[CH2:7][C:6](=[O:37])[O:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 74063781HCID 74063781, compound

Product 1

HCID 86590600HCID 86590600, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-[(Isoquinoline-1-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide, 15, (1.42 g, 2.80 mmol) is stirred in a solution of trifluroacetic acid 5 mL acetonitrile 5 mL, and water 2.5 mL for 2 hours. Solvents are removed in vacuo and the resulting residue dissolved in ethyl acetate and re-concentrated to remove any excess TFA. The crude product is purified over silica (ethyl acetate:0.1% acetic acid,) to afford 1.18 g (78% yield) of the desired product as a yellow foam. 1H NMR (CDCl3): δ 9.30 (m, 1H), 8.85 (d, 7.6 Hz, 1H), 8.48 (d, J=5.4 Hz, 1H), 7.87–7.34 (m, 6H), 5.92–5.71 (m, 3H), 5.54 (m, 1H), 4.71–4.35 (m, 3H), 3.03 (m, 4H), 2.43 (m, 3H), 2.19 (m, 2H), 1.98 (m, 1H). 13C NMR (CDCl3): δ 173.9, 172.5, 171.4, 165.9, 147.9, 140.7, 137.6, 131.4, 130.8, 128.9, 127.5, 127.2, 125.6, 124.9, 61.7, 59.1, 50.4, 34.2, 33.4, 32.3, 27.0. ESI MS 479.11 (M+H). HRMS calc. 479.1931, found 479.1941.

Workup

  1. customSolvents are removed in vacuo
  2. dissolutionthe resulting residue dissolved in ethyl acetate
  3. concentrationre-concentrated
  4. customto remove any excess TFA
  5. customThe crude product is purified over silica (ethyl acetate:0.1% acetic acid,)

Sources & evidence

ORD record
ord-ad39cd784116430c96c08c394cc956f0
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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