Sodium Hydroxide → HCID 178453813, compound

HRID 1879575Notes

Reaction equation

[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]([NH:14][C@@:15]1([C:32]([O:34]CC)=[O:33])[CH2:20][C@@H:19]([S:21][C:22]2[NH:26][CH:25]=[N:24][N:23]=2)[C@@H:18]2[C@H:16]1[C@H:17]2[C:27]([O:29]CC)=[O:28])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCCC1.O>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]([NH:14][C@@:15]1([C:32]([OH:34])=[O:33])[CH2:20][C@@H:19]([S:21][C:22]2[NH:26][CH:25]=[N:24][N:23]=2)[C@@H:18]2[C@H:16]1[C@H:17]2[C:27]([OH:29])=[O:28])=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 2.5 °C

Procedure

Add 2M sodium hydroxide (4.5 mL, 9 mmol) to a stirred solution of diethyl (1R,2S,4R,5R,6R)-2-[[2-(tert-butoxycarbonylamino)acetyl]amino]-4-(4H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate (1.4 g, 2.81 mmol) in tetrahydrofuran (8 mL) at room temperature. Stir the biphasic mixture for 2 hours, dilute the reaction mixture with water (50 mL) and wash with diethyl ether (50 mL). Cool the aqueous layer to 0-5° C., acidify to pH=2 with 2M hydrochloric acid and extract with ethyl acetate (2×60 mL). Combine the organics phases, dry on sodium sulfate and concentrate to give the title compound as a white solid (0.75 g, 1.69 mmol). 1H NMR (D2O) δ 1.18-1.27 (m, 1H), 1.32 (s, 9H), 1.44-1.49 (m, 1H), 2.0-2.6 (m, 1H), 2.12-2.19 (m, 1H), 2.65-2.75 (m, 2H), 3.57-3.68 (m, 2H), 4.12-4.21 (m, 1H), 8.23 (s, 1H) as well as some title compound in the remaining aqueous layer (approximately 1.12 mmol). MS (m/z): 442 (M+1), 464 (M+23).

Workup

washwash with diethyl ether (50 mL)
extractionextract with ethyl acetate (2×60 mL)
customCombine the organics phases, dry on sodium sulfate
concentrationconcentrate

Sources & evidence

ORD record: ord-30960288fe6641c8b40b090b75a8fc35
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318184B2

Reaction notes

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