Triethylamine → HCID 68646337, compound

HRID 339615Notes

Reaction equation

HRID 339615 reaction equation
ClC(OCC)=O.CC[N:9](CC)CC.[OH:14][B:15]1[C:19]2[C:20]([O:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]([CH2:31][N+:32]([O-:34])=[O:33])[O:16]1.[NH4+].[OH-]>C1COCC1>[OH:14][B:15]1[C:19]2[C:20]([O:24][CH2:25][CH2:26][CH2:27][C:28]([NH2:9])=[O:29])=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]([CH2:31][N+:32]([O-:34])=[O:33])[O:16]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 68645793HCID 68645793, compound

Product 1

HCID 68646337HCID 68646337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl chloroformate (80 μL, 0.83 mmol) was added dropwise to a solution of Et3N (0.35 mL, 4.7 mmol) and 4-(1-hydroxy-3-nitromethyl-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-butyric acid (111 mg, 0.38 mmol) in THF (4 mL) at 0° C. (bath temp). The mixture was stirred at 0° C. (bath temp) for 15 min and then 28% NH4OH (0.5 mL) was added dropwise at 0° C. (bath temp). The mixture was allowed to warm to rt over 20 min. The precipitate was isolated by filtration and washed with THF and H2O to give the title compound as a light yellow solid: yield 52 mg (45%).

Workup

  1. temperatureto warm to rt over 20 min
  2. customThe precipitate was isolated by filtration
  3. washwashed with THF and H2O

Sources & evidence

ORD record
ord-19aadb3e4482420c9d6bf60fb9db4460
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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