1,2-Dichloroethane → HCID 57810570, compound

HRID 2106497Notes

Reaction equation

HRID 2106497 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]([OH:30])=O)=[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].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.Cl.C([O:59][C:60](=[O:64])[CH2:61][NH:62][CH3:63])C>>[CH3:34][C:2]1([CH3:1])[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:62]([CH2:61][C:60]([OH:64])=[O:59])[CH3:63])=[O:30])=[CH:25][C:24]=4[CH:31]=3)([CH2:16][CH3:17])[CH2:18][CH3:19])=[CH:11][C:10]=2[CH3:32])[C:3]1=[O:33]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 11167139HCID 11167139, compound

Product 1

HCID 57810570HCID 57810570, compound

Procedure

A solution of 5-{1-[4-(3,3-Dimethyl-2-oxo-cyclohexyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzofuran-2-carboxylic acid (244 mg, 0.527 mmol) (from example 73A), EDC (151 mg, 0.791 mmol), HOBT (75 mg, 0.554 mmol), triethylamine (0.3 ml, 2.1 mmol), and sarcosine ethyl ester hydrochloride (105 mg, 0.685 mmol) were reacted followed by base hydrolysis as in Example 74 to yield (48 mg, 30%) MS (ES) m/e: 532.3 (M−1)

Workup

  1. customfollowed by base hydrolysis as in Example 74
  2. customto yield (48 mg, 30%)

Sources & evidence

ORD record
ord-fe21f2ff6b014b05a5a5bb3409d6505e
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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