Diisopropylcarbodiimide → HCID 178472564, compound

HRID 1514790Notes

Reaction equation

HRID 1514790 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([O:19][C@H:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:21])[C:16](O)=[O:17])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:27][C:28]1[NH:32][N:31]=[N:30][N:29]=1.CCN(C(C)C)C(C)C.C(N=C=NC(C)C)(C)C>C1COCC1>[CH2:25]([O:24][C:22](=[O:23])[C@@H:20]([O:19][C@H:15]([C:16](=[O:17])[NH:27][C:28]1[NH:32][N:31]=[N:30][N:29]=1)[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:9][CH:10]=1)[CH3:21])[CH3:26]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 81531DiisopropylethylamineHCID 58280571HCID 58280571, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178472564HCID 178472564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-(3′-chloro-biphenyl-4-yl)-2-((S)-1-ethoxycarbonyl-ethoxy)-propionic acid (62 mg, 0.165 mmol) in THF (5 ml) at room temperature was added 5-aminotetrazole (38.0 mg, 0.447 mmol), DIPEA (0.086 ml, 0.494 mmol) and followed by 1,3-diisopropylcarbodiimide (0.060 ml, 0.387 mmol). The reaction was stirred at room temperature for 3 hr. The reaction was quenched by brine and was extracted with EtOAc. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated. HPLC retention time=0.99 minutes (condition C); MS (m+1)=444.

Workup

  1. customThe reaction was quenched by brine
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-93f27ea88f9e4b1e991963e4c72a30ba
Source dataset
uspto-grants-2012_07
Patent number
US08222286B2

Reaction notes

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