Diisopropylcarbodiimide → HCID 67332860, compound

HRID 1799800Notes

Reaction equation

HRID 1799800 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:34][C:11]3[C:12](=[O:33])[N:13]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]([OH:30])[CH2:24][S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])=[C:17]([O:31][CH3:32])[CH:16]=4)[CH2:14][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[NH:35]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:36]([C:40](O)=[O:41])[CH:37]([CH3:39])[CH3:38].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:46]([O:45][C:43]([NH:35][C@@H:36]([CH:37]([CH3:39])[CH3:38])[C:40]([O:30][C@H:23]([CH2:24][S:25]([CH2:28][CH3:29])(=[O:26])=[O:27])[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:13]2[CH2:14][C:10]3[CH:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[S:34][C:11]=3[C:12]2=[O:33])=[CH:16][C:17]=1[O:31][CH3:32])=[O:41])=[O:44])([CH3:49])([CH3:48])[CH3:47]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 83693Boc-L-ValineHCID 45280554HCID 45280554, compound

Product 1

HCID 67332860HCID 67332860, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (S)-2-(4-chlorophenyl)-5-(4-(3-(ethylsulfonyl)-2-hydroxypropoxy)-3-methoxyphenyl)-4H-thieno[2,3-c]pyrrol-6(5H)-one) (46.0 mg, 0.088 mmol), DMAP (5.47 mg, 0.045 mmol) and BOC-Val-OH (22.96 mg, 0.106 mmol) in CH2Cl2 (0.401 mL) at RT was added DIC (0.022 mL, 0.141 mmol) dropwise over a period of 1 h. After stirring for an additional 2H, the reaction mixture was filtered and the filtrate was washed with cold 1N HCl (3×10 mL) and cold 10% NaHCO3 (3×10 mL) prior to drying over anhydrous Na2SO4 and concentrating under vacuum. The residue was purified by flash chromatography (silica gel, hexanes:EtOAc, 100:0 to 0:100) to afford 50.4 mg (79% yield) of the title compound as a yellow solid: HPLC retention time: 4.153 min., LCMS (ES): m/z 721 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe filtrate was washed with cold 1N HCl (3×10 mL) and cold 10% NaHCO3 (3×10 mL)
  3. dry with materialto drying over anhydrous Na2SO4
  4. concentrationconcentrating under vacuum
  5. customThe residue was purified by flash chromatography (silica gel, hexanes:EtOAc, 100:0 to 0:100)

Sources & evidence

ORD record
ord-7beb6caa7d244fd293756061d7efce36
Source dataset
uspto-grants-2013_01
Patent number
US08344160B2

Reaction notes

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