Methyl chloroformate → HCID 178502124, compound

HRID 1404372Notes

Reaction equation

HRID 1404372 reaction equation
[OH:1][B:2]1[C@@H:7]([NH:8][C:9](=[O:22])[CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][NH:20]C)[CH2:13][CH2:12]2)[CH2:6][C:5]2[CH:23]=[CH:24][CH:25]=[C:26]([C:27]([OH:29])=[O:28])[C:4]=2[O:3]1.C1COCC1.C([O-])(O)=O.[Na+].Cl[C:41]([O:43][CH3:44])=[O:42]>O.CO>[OH:1][B:2]1[C@@H:7]([NH:8][C:9](=[O:22])[CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][NH:20][C:41]([O:43][CH3:44])=[O:42])[CH2:13][CH2:12]2)[CH2:6][C:5]2[CH:23]=[CH:24][CH:25]=[C:26]([C:27]([OH:29])=[O:28])[C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 178484311HCID 178484311, compound

Product 1

HCID 178502124HCID 178502124, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To (R)-2-hydroxy-3-(2-(trans-4-(2-(methylamino)ethylamino)cyclohexyl)acetamido)-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid from Example 51 (39 mg) in a mixture of H2O (1 mL), THF (1 mL) and MeOH (1 mL) was added NaHCO3 (200 mg), followed by methyl chloroformate (1.2 eq). The reaction mixture was stirred at RT overnight. The solvent was then removed in vacuo and the crude product was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 448 (MH)+.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe crude product was purified by reverse phase preparative HPLC
  3. customdried

Sources & evidence

ORD record
ord-8c80bd33786c47ea8a1e34af4b998bf4
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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