Borane → HCID 86747615, compound

HRID 1975790Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11](O)=O)=[CH:9][C:4]=2[CH2:3][CH2:2]1.ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.C([N:26]([CH2:29]C)[CH2:27]C)C.B.[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[O:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>C(OCC)(=O)C>[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][N:26]([CH2:27][C@H:18]3[C:19]4[C:20](=[C:41]([O:37][CH3:32])[CH:40]=[CH:39][CH:38]=4)[CH2:21][CH2:22][CH2:23]3)[CH3:29])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

2,3-Dihydrobenzofuran-5-acetic acid (0.98 g, 5.5 mmol) and the product from Example 15 (1.21 g, 5.0 mmol) were combined with 1-(3-dmethylaminopropyl)-3-ethyl carbodiimide hydrochloride (1.15 g, 6.0 mmol), 1-hydroxybenzotriazole (1.01 g, 67.5 mmol) and triethylamine (5.5 mmol), 0.7 mL) in tetrahydrofuran (50 mL) and the reaction was stirred for 18 hours at 25° C. The product was isolated and treated with 1.0 M borane in tetrahydrofuran (20 mL) at reflux for 4 hours. After isolation of the desired product, treatment with 1.1 equivalents of methanesulfonic acid and recrystallization from ethyl acetate yielded 1.29 g of the desired product as a white solid. m.p. 161°-163° C. 1H NMR (CDCl3, 300 MHz) δ1.7-2.2 (m, 4H), 2.5-3.7 (m, 9H), 2.86 (s, 3H), 3.00 (d, 3 H), 3.18 (t, 2H), 3.81 (s, 3H), 4.55 (t, 2H), 6.71 (m, 3H), 6.94 (dd, 1H), 7.15 (m, 2H), 10.8 (bs, 1H). Anal calcd for C24H33NO5S: C, 64.40; H, 7.43; N, 3.13. Found: C, 64.33; H, 7.36; N, 3.06.

Workup

customThe product was isolated
temperatureat reflux for 4 hours

Sources & evidence

ORD record: ord-cbba541b3c9d4303b6346f38e6fe4d60
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05288749

Reaction notes

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