Dicyclohexylcarbodiimide → HCID 44603532, compound

HRID 1943319Notes

Reaction equation

HRID 1943319 reaction equation
[O:1]=[C:2]([C@@:17]1([OH:58])[CH2:34][C@H:33]([O:35][C@@H:36]2[O:50][C@@H:49]([CH3:51])[C@H:39]3[O:40][C@H:41]4[N:46]([C@H:38]3[CH2:37]2)[CH2:45][CH2:44][O:43][C@@H:42]4[O:47][CH3:48])[C:32]2[C:19](=[C:20]([OH:57])[C:21]3[C:22](=[O:56])[C:23]4[C:28]([C:29](=[O:53])[C:30]=3[C:31]=2[OH:52])=[C:27]([O:54][CH3:55])[CH:26]=[CH:25][CH:24]=4)[CH2:18]1)[CH2:3][O:4][CH:5]1[O:10][CH:9]([CH2:11][O:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:8][CH2:7][CH2:6]1.O[N:60]1[C:64](=[O:65])[CH2:63][CH2:62][C:61]1=[O:66].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[O:1]=[C:2]([C@@:17]1([OH:58])[CH2:34][C@H:33]([O:35][C@@H:36]2[O:50][C@@H:49]([CH3:51])[C@H:39]3[O:40][C@H:41]4[N:46]([C@H:38]3[CH2:37]2)[CH2:45][CH2:44][O:43][C@@H:42]4[O:47][CH3:48])[C:32]2[C:19](=[C:20]([OH:57])[C:21]3[C:22](=[O:56])[C:23]4[C:28]([C:29](=[O:53])[C:30]=3[C:31]=2[OH:52])=[C:27]([O:54][CH3:55])[CH:26]=[CH:25][CH:24]=4)[CH2:18]1)[CH2:3][O:4][CH:5]1[O:10][CH:9]([CH2:11][O:12][CH2:13][C:14]([O:16][N:60]2[C:64](=[O:65])[CH2:63][CH2:62][C:61]2=[O:66])=[O:15])[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 59184908HCID 59184908, compound

Product 1

HCID 44603532HCID 44603532, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the acid intermediate 49 obtained from step 3 of the process (2 mg, 0.0024 mmol) in dry dichloromethane (1 ml) cooled at 0° C., N-hydroxysuccinimide (1 mg, 0.00792 mmol) and N,N′-dicyclohexylcarbodiimide (1 mg, 0.004556 mmol) were added. The reaction mixture was stirred at 0° C. for 2.5 h, until disappearance of the starting material (HPLC-MS analysis). The solvent evaporated under vacuum and the residue treated with ethyl ether (2×4 ml). The suspension was stirred for 10 minutes, the solid removed by filtration and the organic solution concentrated in vacuo, affording 2 mg of 50 (red solid) as a mixture of diastereoisomers. MS (ESI): 911 [M+H]+. Retention time=6.12, 6.30, 6.42 min (method 1).

Workup

  1. customThe solvent evaporated under vacuum
  2. additionthe residue treated with ethyl ether (2×4 ml)
  3. stirringThe suspension was stirred for 10 minutes
  4. customthe solid removed by filtration
  5. concentrationthe organic solution concentrated in vacuo

Sources & evidence

ORD record
ord-4112672064cf41ffafd2a5256c89800b
Source dataset
uspto-grants-2013_03
Patent number
US08389697B2

Reaction notes

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