Dicyclohexylcarbodiimide → HCID 86666534, compound

HRID 1397121Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].C1CCC(N=C=NC2CCCCC2)CC1>CC#N>[C:31]1(=[O:36])[N:30]([N:24]([C:22](=[O:23])[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:25][C:26]([OH:28])=[O:27])[C:34](=[O:35])[CH2:33][CH2:32]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of acid 58 (887 mg, 2.20 mmol) in dry MeCN (11 mL) at 0° C. was added N-hydroxysuccinimide (278 mg, 2.42 mmol) and DCC (499 mg, 2.42 mmol). After stirring for 4.5 h at 0° C., the reaction mixture was filtered, solids were washed with several small portions of MeCN and the combined filtrates were concentrated to dryness. The crude product was purified by flash chromatography on a Biotage™ flash chromatography system, using a gradient of 60-75% EtOAc in CH2Cl2 as eluent. Evaporation of pure fractions yielded compound 59 (744 mg, 68%) as a white foam. 1H NMR (400 MHz, CDCl3) δ 1.35-1.53 (m, 3H), 1.44 (s, 18H), 1.61-1.71 (m, 2H), 1.83-1.92 (m, 1H), 2.85 (s, 4H), 3.07-3.13 (m, 2H), 4.10-4.15 (m, 1H), 4.40 (d, J=5.7 Hz, 2H), 4.62 (bs, 1H), 5.16 (bs, 1H), 6.86 (bs, 1H).

Workup

filtrationthe reaction mixture was filtered
washsolids were washed with several small portions of MeCN
concentrationthe combined filtrates were concentrated to dryness
customThe crude product was purified by flash chromatography on a Biotage™ flash chromatography system
customEvaporation of pure fractions

Sources & evidence

ORD record: ord-352807cbb1e54bbfb696c2d3e4ffbe7e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901072B2

Reaction notes

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