Dicyclohexylcarbodiimide → HCID 86761365, compound

HRID 1014983Notes

Reaction equation

HRID 1014983 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:32]2([CH3:33])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:34])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@@H:21]([O:23][CH2:24][C:25]([OH:27])=[O:26])[CH3:22])[CH2:12][C@@H:11]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:43][CH2:44][CH:45](O)[CH2:46][CH3:47].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[Si:1]([O:8][C@@H:9]1[C@@:32]2([CH3:33])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:34])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@@H:21]([O:23][CH2:24][C:25]([O:27][CH:45]([CH2:46][CH3:47])[CH2:44][CH3:43])=[O:26])[CH3:22])[CH2:12][C@@H:11]([O:35][Si:36]([C:39]([CH3:41])([CH3:40])[CH3:42])([CH3:37])[CH3:38])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 114283-PentanolHCID 86761364HCID 86761364, compound

Product 1

HCID 86761365HCID 86761365, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

[{1α,3β-Bis(tert-butyldimethylsilyloxy)pregna-5,7-dien-20(S)-yl}oxy]acetic acid (91 mg, 0.147 mmol) was treated with 3-pentanol (39 mg, 0.443 mmol), N,N′-dicyclohexylcarbodiimide (61 mg, 0.296 mmol) and 4-(dimethylamino)pyridine (54 mg, 0.443 mmol) in dichloromethane (1.5 ml) in the same manner as shown in Example 17(3) (at room temperature for 15 hours), followed by work up and purification using preparative thin layer chromatography (0.5 mm×3 plates, hexane:ethyl acetate=5:1, developed once) to give the titled compound (37 mg, 37%) as a colorless oil.

Workup

  1. customas shown in Example 17(3) (at room temperature for 15 hours)
  2. custompurification

Sources & evidence

ORD record
ord-b118c2ada1f94fbe8ae910cf524d63eb
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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