Trifluoroacetic acid → 2,6-Dimethyl-benzoic acid 4-carboxy-3-({6-[(naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carbonyl}-amino)-2-oxo-butyl ester

HRID 1824441Notes

Reaction equation

HRID 1824441 reaction equation
C([O:5][C:6]([CH2:8][CH:9]([NH:24][C:25]([CH:27]1[N:31]2[C:32](=[O:51])[CH:33]([NH:38][C:39]([C:41]3[CH:50]=[CH:49][C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH:42]=3)=[O:40])[CH2:34][CH:35]=[CH:36][CH2:37][CH:30]2[CH2:29][CH2:28]1)=[O:26])[C:10](=[O:23])[CH2:11][O:12][C:13](=[O:22])[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:6]([CH2:8][CH:9]([NH:24][C:25]([CH:27]1[N:31]2[C:32](=[O:51])[CH:33]([NH:38][C:39]([C:41]3[CH:50]=[CH:49][C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH:42]=3)=[O:40])[CH2:34][CH:35]=[CH:36][CH2:37][CH:30]2[CH2:29][CH2:28]1)=[O:26])[C:10](=[O:23])[CH2:11][O:12][C:13](=[O:22])[C:14]1[C:15]([CH3:21])=[CH:16][CH:17]=[CH:18][C:19]=1[CH3:20])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69584372HCID 69584372, compound

Product 1

HCID 695844402,6-Dimethyl-benzoic acid 4-carboxy-3-({6-[(naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carbonyl}-amino)-2-oxo-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dimethyl-benzoic acid 4-tert-butoxycarbonyl-3-({6-[(naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carbonyl}-amino)-2-oxo-butyl ester, 112, (188 mg 0.27 mmol) is treated with solution of trifluoroacetic acid (10 ml) and dichloromethane (10 ml). The mixture is stirred for 2 hours and solvent is removed in vacuo. The residue is purified over silica (dichloromethane/methanol 95:5) to afford 120 mg of the desired product as a white solid. 1H NMR (CDCl3): δ 8.32 (d, J=5.9 Hz, 1H), 7.84 (m, 4H), 7.71 (m, 1H), 7.51 (m, 2H), 7.23 (dd, J-16.1, 8.1 Hz, 1H), 7.04 (t, J=7.4 Hz, 1H), 5.87 (m, 2H), 5.65 (m, 2H), 5.13–4.80 (m, 3H), 4.51 (m, 1H), 4.24 (m, 1H), 3.02–2.86 (m, 4H), 2.37 (s, 6H), 2.43–1.83 (m, 5H). 13C NMR (CDCl3): δ 200.4, 200.1, 174.2, 172.9, 171.6, 171.4, 169.3, 167.6, 135.9, 135.1, 132.7, 131.2, 130.8, 129.9, 129.3, 128.7, 128.4, 128.3, 127.9, 127.0, 126.1, 125.7, 123.9, 66.9, 62.3, 61.7, 59.4, 59.1, 53.2, 52.9, 50.8, 35.3, 34.4, 34.2, 33.3, 32.2, 27.4, 26.9, 20.1. (excess carbons due to rotamers). ESI MS 639.69 (M+H).

Workup

  1. customsolvent is removed in vacuo
  2. customThe residue is purified over silica (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-974457ac4a0e42988a4141e4347fdfe1
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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