Triethylamine → HCID 58333373, compound

HRID 2066858Notes

Reaction equation

HRID 2066858 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([C:28](O)=[O:29])=[CH:23][C:22]=3[F:31])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.O.C([O-])(O)=O.[Na+]>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][OH:29])=[CH:23][C:22]=3[F:31])[CH2:19][CH2:20]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 58333593HCID 58333593, compound

Product 1

HCID 58333373HCID 58333373, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 40 mg of 9-1 (0.09 mmol) and triethylamine (20 μL, 0.13 mmol) in 1 mL of THF at 0° C., was added ethyl chloroformate (12 μL, 0.13 mmol). The mixture was stirred at room temperature for 4 h then added to a stirred suspension of NaBH4 (15 mg, 0.39 mmol) in water (0.5 mL). After 1 h of stirring, the mixture was diluted with aqueous NaHCO3 (4 mL) and extracted with ethyl acetate (2×4 mL). The combined extracts were dried under a stream of nitrogen and the residue was purified by preparative HPLC to afford 48-1: LC-MS 408.1 (MH+-18).

Workup

  1. stirringAfter 1 h of stirring
  2. extractionextracted with ethyl acetate (2×4 mL)
  3. customThe combined extracts were dried under a stream of nitrogen
  4. customthe residue was purified by preparative HPLC
  5. customto afford 48-1

Sources & evidence

ORD record
ord-e2452c6f66cb4e78b3483a9115344e4f
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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