Dicyclohexylcarbodiimide → HCID 69883340, compound

HRID 2120549Notes

Reaction equation

[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[N:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23].C1CCC(N=C=NC2CCCCC2)CC1>COCCOC>[CH3:7][C:4]([CH3:5])([O:3][C:1]([NH:8][C@H:9]([C:13]([CH:19]1[CH2:20][C:21](=[O:22])[NH:17][C:18]1=[O:23])=[O:15])[CH:10]([CH3:11])[CH3:12])=[O:2])[CH3:6]

Participants

Conditions

Temperature: 5 °C

Procedure

To a cooled (icebath) stirred solution of BOC—L-valine (4.56 g, 0.021 mol), and N-hydroxysuccinimide (2.41 g, 0.021 mol) in DME (50 mL) was added DCC (4.75 g, 0.023 mol). The reaction was stirred for 6 h at 5° C. and then left to stand in the refrigerator over night. The reaction was then cold filtered, washing with Et2O, and conc to yield a solid which was crystallized from EtOAc/hexane to give the desired product as a white crystalline sold (4.59 g, 69.5%): mp 123-124° C.; 1H NMR (300 MHz, CDCl3) δ 5.00-4.95 (d, 1H, J=9.3 Hz), 4.62 (dd, 1H, J=4.97 Hz), 2.85 (s, 4H), 2.75-2.44 (m, 1H), 1.45 (s, 9H), 1.25-0.90 (m, 6H); 13C NMR (CDCl3) δ 168.6, 167.9, 155.1, 155.0, 80.4, 77.4, 77.2, 77.0, 76.6, 76.5, 57.0, 31.6, 31.1, 28.2, 28.1, 28.0, 27.99, 27.93, 25.5, 18.6, 17.3; MS (Cl/CH4) m/z 315 (MH+), 299, 287, 259, 241, 215 (base peak), 173, 172, 145, 144, 116, 100, 72. Anal. Calcd. for C14H22N2O6: C, 53.49; H, 7.05; N, 8.91. Found: C, 53.67; H, 7.06; N, 8.81.

Workup

temperatureTo a cooled (icebath)
waitleft
waitto stand in the refrigerator over night
washcold filtered, washing with Et2O
customconc to yield a solid which
customwas crystallized from EtOAc/hexane

Sources & evidence

ORD record: ord-43b321633ae84f0c818ef51955967cd6
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693072B2

Reaction notes

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