HCID 178434150, compound → HCID 178434151, compound

HRID 929907Notes

Reaction equation

HRID 929907 reaction equation
C([O:5][C:6]([C@:8]1([NH:28]C(OC(C)(C)C)=O)[CH2:13][C@@H:12]([S:14][C:15]2[NH:19][C:18]([CH3:20])=[N:17][N:16]=2)[C@@H:11]2[C@H:9]1[C@H:10]2[C:21]([O:23]C(C)(C)C)=[O:22])=[O:7])(C)(C)C>O>[NH2:28][C@@:8]1([C:6]([OH:7])=[O:5])[CH2:13][C@@H:12]([S:14][C:15]2[NH:19][C:18]([CH3:20])=[N:17][N:16]=2)[C@@H:11]2[C@H:9]1[C@H:10]2[C:21]([OH:23])=[O:22]

Participants

3

Reactant 1

HCID 178434150HCID 178434150, compound

Product 1

HCID 178434151HCID 178434151, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Dissolve ditert-butyl(1R,2S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-4-[(5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate (85 mg, 0.166 mmol) acetic acid (1 mL) and water (1 mL). Heat the mixture to 160° C. at approximately 40 Watts in a BIOTAGE® Initiator microwave for 6 minutes. Concentrate reaction mixture under reduced pressure. Add water and remove under reduced pressure twice to remove excess acetic acid to give the title compound as a white solid (40 mg, 88.6%). MS (m/z): 299 (M+1).

Workup

  1. concentrationConcentrate
  2. customreaction mixture under reduced pressure
  3. customAdd water and remove under reduced pressure twice
  4. customto remove excess acetic acid

Sources & evidence

ORD record
ord-1378cd06317a4f9ba913f5ba08f84421
Source dataset
uspto-grants-2016_03
Patent number
US09296710B2

Reaction notes

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