Dicyclohexylcarbodiimide → HCID 86665801, compound

HRID 1943316Notes

Reaction equation

HRID 1943316 reaction equation
[O:1]=[C:2]([C@@:16]1([OH:57])[CH2:33][C@H:32]([O:34][C@@H:35]2[O:49][C@@H:48]([CH3:50])[C@H:38]3[O:39][C@H:40]4[N:45]([C@H:37]3[CH2:36]2)[CH2:44][CH2:43][O:42][C@@H:41]4[O:46][CH3:47])[C:31]2[C:18](=[C:19]([OH:56])[C:20]3[C:21](=[O:55])[C:22]4[C:27]([C:28](=[O:52])[C:29]=3[C:30]=2[OH:51])=[C:26]([O:53][CH3:54])[CH:25]=[CH:24][CH:23]=4)[CH2:17]1)[CH2:3][O:4][C:5]1([O:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.O[N:59]1[C:63](=[O:64])[CH2:62][CH2:61][C:60]1=[O:65].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[O:1]=[C:2]([C@@:16]1([OH:57])[CH2:33][C@H:32]([O:34][C@@H:35]2[O:49][C@@H:48]([CH3:50])[C@H:38]3[O:39][C@H:40]4[N:45]([C@H:37]3[CH2:36]2)[CH2:44][CH2:43][O:42][C@@H:41]4[O:46][CH3:47])[C:31]2[C:18](=[C:19]([OH:56])[C:20]3[C:21](=[O:55])[C:22]4[C:27]([C:28](=[O:52])[C:29]=3[C:30]=2[OH:51])=[C:26]([O:53][CH3:54])[CH:25]=[CH:24][CH:23]=4)[CH2:17]1)[CH2:3][O:4][C:5]1([O:11][CH2:12][C:13]([O:15][N:59]2[C:63](=[O:64])[CH2:62][CH2:61][C:60]2=[O:65])=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 59184940HCID 59184940, compound

Product 1

HCID 86665801HCID 86665801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the acid intermediate 46 (4 mg, 0.005 mmol) in dry Dichloromethane (2 mL) kept at +5° C., N-hydroxysuccinimide (2 mg, 0.017 mmol) and N,N′-dicyclohexylcarbodiimide (2 mg, 0.01 mmol) were added. The solution was stirred at room temperature for 6 h, the solvent evaporated under vacuum and the residue treated with ethyl ether (5 mL). The suspension was stirred for 30 minutes, the solid removed by filtration and organic solution concentrated in vacuo. Purification of the crude by flash chromatography (DCM/Acetone 80:20) yield 1.5 mg (y=33%) of 47 as a red solid. MS (ESI): 895 [M+H]+. Retention time=3.22 min. Method 1.

Workup

  1. customkept at +5° C.
  2. customthe solvent evaporated under vacuum
  3. additionthe residue treated with ethyl ether (5 mL)
  4. stirringThe suspension was stirred for 30 minutes
  5. customthe solid removed by filtration and organic solution
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude by flash chromatography (DCM/Acetone 80:20) yield 1.5 mg (y=33%) of 47 as a red solid

Sources & evidence

ORD record
ord-e3ecfd8024a1495283294bbeda5692f8
Source dataset
uspto-grants-2013_03
Patent number
US08389697B2

Reaction notes

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