Hydrochloric Acid → 2-[5-(Naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyrimidine-5-carboxylic acid

HRID 2079818Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][CH:17]2[CH2:19][N:20]([C:22]3[N:27]=[CH:26][C:25]([C:28]([O:30]CC)=[O:29])=[CH:24][N:23]=3)[CH2:21][CH:16]2[CH2:15]1)(=[O:13])=[O:12].[OH-].[Na+].Cl>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:15][CH:16]2[CH2:21][N:20]([C:22]3[N:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][N:23]=3)[CH2:19][CH:17]2[CH2:18]1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of ethyl 2-[5-(naphthalene-2-sulfonyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-pyrimidine-5-carboxylate (0.201 g, 0.44 mmol) in ethanol (2 ml) was added 6M NaOH solution (2 ml, 12 mmol). The reaction was heated at 80° C. for 2 h, then cooled to r.t. The pH was adjusted to ˜5 by addition of 2M HCl. The solution was allowed to stand overnight, and the product was collected by filtration to give the title compound (0.154 g, 82%). 1H NMR (300 MHz, d6-DMSO) δ: 2.80-2.95 (2H, m), 3.17 (2H, dd, J=3.6, 10.2 Hz), 3.20-3.30 (2H, m), 3.46 (2H, dd J=7.2, 10.5 Hz), 3.61 (2H, dd, J=6.9, 11.7 Hz), 7.60-7.78 (2H, m), 7.82 (1H, dd, J=1.8, 8.7 Hz), 8.06 (1H, d, J=8.1 Hz), 8.13 (1H, d, J=8.7 Hz), 8.18 (1H, d, J=7.8 Hz), 8.47 (1H, s), 8.59 (2H, s).

Workup

temperaturecooled to r.t
filtrationthe product was collected by filtration

Sources & evidence

ORD record: ord-d59355d7942f4f4b8074cec46d464eab
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932246B2

Reaction notes

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