Dimethylformamide → HCID 71116073, compound

HRID 1771081Notes

Reaction equation

[CH2:1]([SH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[H-].[Na+].CCO[C:16]([CH3:18])=[O:17].[CH3:19][CH2:20][CH2:21]CCC.C[N:26](C=O)C>>[CH2:1]([S:10][CH2:19][CH:20]1[NH:26][C:16](=[O:17])[CH2:18][CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 4

HCID 6228Dimethylformamide3×

HCID 150771-Nonanethiol

HCID 24758Sodium hydride

HCID 21226206Ethyl acetate hexane

Product 1

HCID 71116073HCID 71116073, compound

Procedure

Treatment of 6 (17) [(5S), 458 mg, 2.58 mmol] in dry DMF (3 mL) with thiolate solution in dry DMF (7 mL) generated from nonanethiol (510 μL, 433 mg, 2.71 mmol), and NaH (114 mg, 2.84 mmol, 60%/mineral oil) in dry DMF (7 mL) by Procedure A [column chromatography (80% EtOAc/hexane→EtOAc)] gave 7c(5S) (652 mg, 98%) as a colorless oil: 1H NMR δ 0.86 (t, J=7.0 Hz, 3H), 1.19-1.29 (m, 10H), 1.29-1.38 (m, 2H), 1.54 (‘quint’, J=7.3 Hz, 2H), 1.75-1.85 (m, 1H), 2.23-2.43 (m, 3H), 2.51 (t, J=7.5 Hz, 2H), 2.54 (dd, J=7.4, 13.2 Hz, 1H), 2.65 (dd, J=5.8, 13.2 Hz, 1H), 3.78 (‘quint’, J=6.5 Hz, 1H), 6.97 (br. s, 1H); 13C NMR δ 14.1, 22.6, 26.6, 28.8, 29.2, 29.2, 29.4, 29.8, 30.1, 31.8, 32.7, 38.6, 53.9, 178.0; MS (ESI) m/z 258 (100, M+).

Workup

customgave 7c(5S) (652 mg, 98%) as a colorless oil

Sources & evidence

ORD record: ord-0edb8f0c08954ac9ae2b59dce9fcfcfa
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249095B2

Reaction notes

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