Toluene → HCID 58979698, compound

HRID 1180761Notes

Reaction equation

[N:1]([C@@H:4]([CH2:8][CH2:9][CH2:10][CH3:11])[C:5]([O-:7])=[O:6])=[C:2]=[O:3].[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]1.[C:27]1(C)C=CC=CC=1>>[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1([O:26][C:2]([NH:1][C@@H:4]([CH2:8][CH2:9][CH2:10][CH3:11])[C:5]([O:7][CH3:27])=[O:6])=[O:3])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Reactant 3

HCID 1140Toluene

HCID 12399387HCID 12399387, compound

HCID 86597004HCID 86597004, compound

Product 1

HCID 58979698HCID 58979698, compound

Conditions

Temperature: 80 °C

Procedure

1.7 g (9.9 mmol) of (2S)-2-isocyanatohexanoate and 2.0 g (9.1 mmol) of 1-(1,3-benzothiazol-2-yl)cyclopentanol were dissolved in 5 mL of dry toluene and heated at 80° C. for 4 d. After removal of solvent, purification by silica gel column chromatography eluting with hexane:ethyl acetate (2:1) gave 3.5 g of methyl(2S)-2-[({[1-(1,3-benzothiazol-2-yl)cyclopentyl]oxy}carbonyl)amino]hexanoate as a yellow liquid, quantitatively. 1H NMR (300 MHz, CDCl3) δ 8.02 (d, J=8 Hz, 1H), 7.86 (d, J=8 Hz, 1H), 7.47 (t, J=8 Hz, 1H), 7.37 (t, J=8 Hz, 1H), 5.42 (d J=8 Hz, 1H), 4.30 (m, 1H), 3.76 (s, 3H), 2.50 (m, 2H), 1.67-2.08 (m, 6H), 1.30 (m, 6H), 0.92 (t, J=8 Hz, 3H).

Workup

customAfter removal of solvent, purification by silica gel column chromatography
washeluting with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record: ord-62f0067311614d8a87a5ec8338abc9a3
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282512B2

Reaction notes

Loading…