Dicyclohexylcarbodiimide → HCID 117831408, compound

HRID 525314Notes

Reaction equation

HRID 525314 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][N:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23].[CH2:24]([C:52]([OH:54])=[O:53])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([C:49](O)=[O:50])([C:46]([OH:48])=[O:47])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH:44]=[CH2:45]>C(Cl)Cl.C1COCC1>[O:23]=[C:18]1[CH2:19][CH2:20][C:21](=[O:22])[N:17]1[O:16][C:49]([C:34]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH:44]=[CH2:45])([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:52]([OH:54])=[O:53])[C:46]([OH:48])=[O:47])=[O:50]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 117831398HCID 117831398, compound2×

Product 1

HCID 117831408HCID 117831408, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

DCC (187 mg, 0.908 mmol) in DCM (2 mL) was added to a solution of N-hydroxysuccinimide (99 mg, 0.862 mmol) and docos-21-ene-1,11,11-tricarboxylic acid (Intermediate 45: 400 mg, 0.908 mmol) in DCM (7 mL) and THF (0.7 mL). The reaction was stirred overnight before the solvent was evaporated. The residue was purified by HPLC (Sunfire C18 30×50 mm; 55-80% ACN/water+0.1% TFA) to yield the title compound (155 mg, 0.288 mmol, 32%): by LCMS Method D Rt=1.51 min, M+H 538.3; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.16-1.46 (m, 28 H) 1.60-1.87 (m, 3 H) 1.91-2.17 (m, 5 H) 2.38 (t, J=7.03 Hz, 2 H) 2.86 (br. s., 4 H) 3.68 (dd, J=11.25, 7.34 Hz, 1 H) 3.78 (dd, J=11.31, 5.20 Hz, 1 H) 3.99-4.10 (m, 1 H).

Workup

  1. customwas evaporated
  2. customThe residue was purified by HPLC (Sunfire C18 30×50 mm; 55-80% ACN/water+0.1% TFA)

Sources & evidence

ORD record
ord-78d6ec8ad932435791861c3b8005ed9a
Source dataset
uspto-grants-2016_05
Patent number
US09340582B2

Reaction notes

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