tert-Butyl carbamate → HCID 145857648, compound

HRID 723233Notes

Reaction equation

[C:1]([O:5][C:6](=[O:8])[NH2:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[CH3:14][S:15][C:16]1[S:20][C:19]([C:21]#[N:22])=[CH:18][C:17]=1[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:27]=1)(=[O:25])=[O:24]>C1COCC1>[C:1]([O:5][C:6](=[O:8])[NH:7][C:21](=[NH:22])[C:19]1[S:20][C:16]([S:15][CH3:14])=[C:17]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH:27]=2)(=[O:25])=[O:24])[CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of carbamic acid tert-butyl ester (8 mg, 0.069 mmol, Aldrich Chemical Company) in 1 mL of THF at −78° C. was added 35 uL of n-BuLi under Ar. The mixture was stirred at −78° C. for 15 min. A solution of 5-methylsulfanyl-4-(3-piperidin-1-yl-benzenesulfonyl)-thiophene-2-carbonitrile (20 mg, 0.053 mmol, Example 286: step g) in 1 mL of THF was added. The resulting mixture was stirred at RT for 5 h, then at 50° C. overnight. Cooled to RT, the mixture was purified directly by PTLC (20% EtOAc/hexane) to give 10 mg (38%) of product as colorless oil: 1H-NMR (CDCl3; 400 MHz) δ 8.42 (s, 1H), 7.74 (dd, 1H, J=1.6, 1.6 Hz), 7.67 (s, 1H), 7.62 (ddd, 1H, J=7.5, 1.6, 1.6 Hz), 7.57 (d, 1H, J=7.5, 1.6, 1.6 Hz), 7.52 (dd, 1H, J=7.5, 7.5), 3.42–3.40 (m, 4H), 2.54 (s, 3H), 1.64 (br s, 6H), 1.61 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C22H29N3O4S3, 496.1 (M+H), found 495.9.

Workup

stirringThe resulting mixture was stirred at RT for 5 h
customat 50° C.
customovernight
temperatureCooled to RT
customthe mixture was purified directly by PTLC (20% EtOAc/hexane)

Sources & evidence

ORD record: ord-5223b8e8a83845d998384856e126dd34
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

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