Dicyclohexylcarbodiimide → HCID 11648626, compound

HRID 1685534Notes

Reaction equation

HRID 1685534 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:46]([O:48][C:49](=[O:58])[CH2:50][C:51]1[N:52]=[C:53]([NH2:57])[S:54][C:55]=1[CH3:56])[CH3:47].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH2:46]([O:48][C:49](=[O:58])[CH2:50][C:51]1[N:52]=[C:53]([NH:57][C:8](=[O:10])[CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[S:54][C:55]=1[CH3:56])[CH3:47]

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 120694893-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acidHCID 18526060ethyl 2-(2-amino-5-methylthiazol-4-yl)acetate

Product 1

HCID 11648626HCID 11648626, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyclopentyl-2-(4-methanesulfonylphenyl)propionic acid (200 mg, 0.67 mmol) in a mixture of dry methylene chloride (5 mL) and dry DMF (1 mL) were added HOBT (20 mg) and DCC (155 mg, 0.75 mmol), and the mixture was stirred at room temperature for 2 h. A solution of (2-amino-5-methyl-thiazol-4-yl)-acetic acid ethyl ester (220 mg, 0.78 mmol) and DIPEA (135 μl, 102 mg, 0.79 mmol) in dry DMF (1 mL) was added to the reaction mixture and stirring was continued for 18 h at room temperature. The mixture was evaporated in vacuo and the residue purified on a silica gel column (heptan:ethyl acetate (7:3)) to give {2-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionylamino]-5-methyl-thiazol-4-yl}-acetic acid ethyl ester. Yield: 120 mg (37%). 1H-NMR (CDCl3): δ 8.86 (broad s, 1H), 7.91 (d, 2H), 7.52 (d, 2H), 4.14 (q, 2H), 3.66 (t, 1H), 3.57 (s, 2H), 3.07 (s, 3H), 2.32 (s, 3H), 2.25-2.18 (m, 1H), 1.93-1.86 (m, 1H), 1.81-1.43 (m, 7H), 1.24 (t, 3H), 1.16-1.06 (m, 2H); HPLC-MS: m/z=480 (M+1); Rt=4.09 min.

Workup

  1. stirringstirring
  2. waitwas continued for 18 h at room temperature
  3. customThe mixture was evaporated in vacuo
  4. customthe residue purified on a silica gel column (heptan:ethyl acetate (7:3))

Sources & evidence

ORD record
ord-efad11f383a44b358775a937763c5b1b
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

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