Water → 1-(2-Nitro-benzenesulfonyl)-4-[(thymin-1-yl)-acetyl]-piperazin-2-one

HRID 1794946Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][N:16]([C:21](=[O:32])[CH2:22][N:23]1[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]1=[O:25])[CH2:17][C:18](O)=[O:19])(=[O:12])=[O:11])([O-:3])=[O:2].CN1CCOCC1.O>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:14][CH2:15][N:16]([C:21](=[O:32])[CH2:22][N:23]2[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:17][C:18]1=[O:19])(=[O:11])=[O:12])([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-N-[(thymin-1-yl)-acetyl]-glycine (469 mg, 1.0 mmol) and N-mehtyl morpholine (330 μL, 3 mmol) in THF (10 mL) was added isobutylchloroformatre (205 mg, 1.5 mmol) at −20° C. The reaction mixture was allowed to warm to 0° C. for a period of 1 h. Then water (10 mL) was added to the reaction mixture to precipitate solid. The solid was filtered off, washed with water, dried in vacuo to give the tiltled compound (442 mg, 98%). 1H-NMR (500 MHz; DMSO-d6) δ 11.32 (s, 0.6H), 11.30 (s, 0.4H), 8.35 (m, 1H), 8.12 (dd, 1H), 8.04˜7.96 (m, 2H), 7.35 (s, 0.6H), 7.28 (s, 0.4H), 4.67 (s, 1.2H), 4.59 (s, 0.8H), 4.41 (s, 0.8H), 4.27 (s, 1.2H), 4.04 (m, 1.2H), 3.95 (m, 1.2H), 3.90˜3.85 (m, 1.6H), 1.75 (s, 3H).

Workup

customto precipitate solid
filtrationThe solid was filtered off
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-19a59228a20f47a0b2c240bd545c2102
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022851B2

Reaction notes

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