Dimethylformamide → HCID 71116009, compound

HRID 1771080Notes

Reaction equation

[CH2:1]([SH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].CCO[C:13]([CH3:15])=[O:14].[CH3:16][CH2:17][CH2:18]CCC.C[N:23](C=O)C>>[CH2:1]([S:7][CH2:16][CH:17]1[NH:23][C:13](=[O:14])[CH2:15][CH2:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Reactant 4

HCID 6228Dimethylformamide2×

HCID 81061-Hexanethiol

HCID 24758Sodium hydride

HCID 21226206Ethyl acetate hexane

Product 1

HCID 71116009HCID 71116009, compound

Procedure

Treatment of 6 (17) [(5S), 823 mg, 4.62 mmol] in dry DMF (6 mL) with a thiolate solution in dry DMF (6 mL) generated from hexanethiol (682 μL, 573 mg, 4.86 mmol), and NaH (204 mg, 5.09 mmol, 60%/mineral oil) by Procedure A [column chromatography (80% EtOAc/hexane→5% MeOH/EtOAc)] gave 7b(5S) (932 mg, 94%) as a colorless oil: 1H NMR δ 0.90 (t, J=7.0 Hz, 3H), 1.24-1.33 (m, 4H), 1.33-1.42 (m, 2H), 1.58 (‘quint’, J=7.4 Hz, 2H), 1.78-1.87 (m, 1H), 2.27-2.46 (m, 3H) 2.53 (dd, J=8.0, 13.4 Hz, 1H), 2.54 (t, J=7.3 Hz, 2H), 2.70 (dd, J=5.3, 13.2 Hz, 1H), 3.81 (‘quint’, J=6.6 Hz, 1H), 6.47 (br. s, 1H); 13C NMR δ 14.0, 22.5, 26.8, 28.5, 29.7, 30.1, 31.4, 32.7, 38.7, 53.8, 177.7; MS (ESI) m/z 216 (100, M+).

Workup

customgave 7b(5S) (932 mg, 94%) as a colorless oil

Sources & evidence

ORD record: ord-022bc55d754d487d907ccb6b0552cccd
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249095B2

Reaction notes

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