Benzene → HCID 11253896, compound

HRID 731323Notes

Reaction equation

[CH3:1][Si](C=[N+]=[N-])(C)C.C(OCC)C.[C:13]([O:17][C:18]([NH:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]1[C:27]([OH:29])=[O:28])=[O:19])([CH3:16])([CH3:15])[CH3:14].C1C=CC=CC=1>CO>[CH3:1][O:28][C:27]([C@H:22]1[CH2:23][CH2:24][CH2:25][CH2:26][C@H:21]1[NH:20][C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19])=[O:29]

Participants

Conditions

Temperature: 25 °C

Procedure

A 2.0 M solution of (trimethylsilyl)diazomethane in diethyl ether (5.0 mL, 10.0 mmol) was added over 10 min to a solution of (1S,2R)-2-tert-butoxycarbonylamino-1-cyclohexanecarboxylic acid (0.994 g, 4.09 mmol; purchased from NeoMPS) in a 1:1 mixture of benzene and methanol (50 mL) at 25° C. The resulting mixture was stirred at 25° C. for 30 min, and then was partitioned between half-saturated sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL). The combined organic layers were dried over sodium sulfate, decanted, and were concentrated in vacuo to afford the desired product, (1S,2R)-2-tert-butoxycarbonylamino-1-cyclohexanecarboxylic acid methyl ester (1.00 g, 3.89 mmol, 95%), as a colorless oil. 1H NMR (400 MHz, CDCl3) δ: 1.44 (9H, s), 1.58-1.68 (3H, m), 1.72-1.81 (2H, m), 1.98-2.05 (2H, m), 2.77-2.80 (1H, m), 3.69 (3H, s), 3.82-3.90 (1H, m), 5.29-5.31 (1H, m). LC-MS (ESI) calcd for C13H23NO4 257.16, found 258.2 [M+H+].

Workup

customwas partitioned between half-saturated sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
customdecanted
concentrationwere concentrated in vacuo

Sources & evidence

ORD record: ord-05fa3502f7394f32a4cbc89d4a4dcdba
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582626B2

Reaction notes

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