Sodium Hydroxide → HCID 178444618, compound

HRID 717323Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@:9]([OH:29])([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:17]=3[N:16]=2)[C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.[N:30]([C@@H:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH3:34])=[C:31]=[O:32].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@:9]2([C:15]3[NH:19][C:18]4[CH:20]=[CH:21][C:22]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][C:17]=4[N:16]=3)[O:29][C:31](=[O:32])[N:30]([C@@H:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH3:34])[C:10]2=[O:12])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (R)-ethyl 3-(4-fluorophenyl)-2-hydroxy-2-(5-(methylsulfonamido)-1H-benzo[d]imidazol-2-yl)propanoate (50 mg, 0.12 mmol) in THF (0.5 ml) at rt were added (R)-2-isocyanatoheptane (25 mg, 0.18 mmol) and NaOH (6 mg, 0.15 mmol). The mixture was heated at 70° C. for 25 min. The resulting mixture was filtered through a short plug of silica and concentrated. The resulting residue was purified by Combiflash (silica gel column, 5-35% ethyl acetate in hexane) to give the title product. LC/MS (m/z): 517.0 [M+1]; 1H NMR (400 MHz, CDCl3) δ 10.8-10.9 (d, 1H), 7.6 (t, 1H), 7.5 (s, 1H), 7.3 (m, 1H), 7.2 (m, 2H), 6.9 (m, 2H), 3.7-3.8 (m, 2H), 3.5 (d, 1H), 2.9 (s, 3H), 1.3 (q, 2H), 0.9-1.1 (m, 5H), 0.6-0.9 (m, 7H);

Workup

filtrationThe resulting mixture was filtered through a short plug of silica
concentrationconcentrated
customThe resulting residue was purified by Combiflash (silica gel column, 5-35% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-afede7294f874415adbd8870f2c7e43b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193717B2

Reaction notes

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