Diisopropylcarbodiimide → HCID 66699557, compound

HRID 1818491Notes

Reaction equation

HRID 1818491 reaction equation
CC([N:4]=C=NC(C)C)C.[C:10]([C:13]1[CH:45]=[CH:44][C:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([O:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][O:39]3)[C:26]3[CH:27]=[CH:28][C:29]([O:35][CH3:36])=[C:30]([CH:34]=3)[C:31](O)=[O:32])=[CH:21][CH:20]=2)=[C:15]([CH2:46][CH2:47][CH3:48])[C:14]=1[OH:49])(=[O:12])[CH3:11].O.ON1C2C=CC=CC=2N=N1>ClCCl>[C:10]([C:13]1[CH:45]=[CH:44][C:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([O:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][O:39]3)[C:26]3[CH:27]=[CH:28][C:29]([O:35][CH3:36])=[C:30]([CH:34]=3)[C:31]([NH2:4])=[O:32])=[CH:21][CH:20]=2)=[C:15]([CH2:46][CH2:47][CH3:48])[C:14]=1[OH:49])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66699547HCID 66699547, compound

Product 1

HCID 66699557HCID 66699557, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add N,N-diisopropylcarbodiimide (0.114 g, 0.902 mmol) to a solution of 5-[[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-2-methoxy-benzoic acid (0.450 g, 0.820 mmol) and 1-hydroxybenzotriazole hydrate (0.122 g, 0.902 mmol) in dichloromethane (0.2M). Stir the solution for 1 h at room temperature. Saturate the solution with ammonia gas and stir the solution for 24 h. Collect the precipitate as the title compound (0.440 g, 0.815 mmol, 98%): MS (m/z): 546 (M−1).

Workup

  1. concentrationSaturate the solution with ammonia gas
  2. stirringstir the solution for 24 h

Sources & evidence

ORD record
ord-fb456a2b945d4fb1894824f098fb723c
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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