1,2-Dichloroethane → HCID 57810584, compound

HRID 2106498Notes

Reaction equation

HRID 2106498 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][CH2:5][CH:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:20]3[CH:21]=[CH:22][C:23]4[O:27][C:26]([C:28](O)=[O:29])=[CH:25][C:24]=4[CH:31]=3)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=2[CH3:32])[C:3]1=[O:33].[CH2:35](Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.Cl.C[O:58][C:59](=[O:65])[C@H:60]([CH:62]([CH3:64])[CH3:63])[NH2:61]>>[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][CH2:5][CH:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:20]3[CH:21]=[CH:22][C:23]4[O:27][C:26]([C:28]([N:61]([CH3:35])[CH:60]([CH:62]([CH3:64])[CH3:63])[C:59]([OH:58])=[O:65])=[O:29])=[CH:25][C:24]=4[CH:31]=3)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=2[CH3:32])[C:3]1=[O:33]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 111190Methyl valinate hydrochlorideHCID 11167139HCID 11167139, compound

Product 1

HCID 57810584HCID 57810584, compound

Procedure

A solution of 5-{1-[4-(3,3-Dimethyl-2-oxo-cyclohexyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzofuran-2-carboxylic acid (100 mg, 0.204 mmol) (from example 73A), EDC (58 mg, 0.306 mmol), HOBT (32 mg, 0.244 mmol), triethylamine (0.1 ml, 0.816 mmol), and L-valine methyl ester hydrochloride (41 mg, 0.244 mmol) were reacted followed by base hydrolysis as in Example 74 to yield (80 mg, 68%) MS (ES) m/e: 574.3 (M−1)

Workup

  1. customfollowed by base hydrolysis as in Example 74
  2. customto yield (80 mg, 68%)

Sources & evidence

ORD record
ord-d358295d15e9451ea861cd99aa566966
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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