Acetic Acid → HCID 66823319, compound

HRID 473588Notes

Reaction equation

HRID 473588 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([N:13]3[CH2:16][C:15](=O)[CH2:14]3)=[O:12])[S:8][C:7]=2[CH:18]=1.[C:21]([NH:28][CH2:29][CH2:30][NH2:31])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[C:24]([O:23][C:21](=[O:22])[NH:28][CH2:29][CH2:30][NH:31][CH:15]1[CH2:16][N:13]([C:11]([C:9]2[S:8][C:7]3[CH:18]=[C:3]([C:2]([F:20])([F:19])[F:1])[CH:4]=[CH:5][C:6]=3[CH:10]=2)=[O:12])[CH2:14]1)([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 66823529HCID 66823529, compound

Product 1

HCID 66823319HCID 66823319, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 1e (62 mg, 0.207 mmol), N-Boc-ethylenediamine 1f (100 mg, 0.62 mmol), and acetic acid (0.3 mL) in 1,2-dichloroethane (3 mL) was added Na(OAc)3BH (53 mg, 0.25 mmol). The reaction mixture was stirred at room temperature overnight, and was then quenched with aq. NaHCO3. The resulting mixture was extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 4% MeOH/CH2Cl2) gave intermediate 1g as colorless oil (30 mg).

Workup

  1. customwas then quenched with aq. NaHCO3
  2. extractionThe resulting mixture was extracted with CH2Cl2
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography (silica gel, 4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-085b8ba409d449f7bb547aa4107d197c
Source dataset
uspto-grants-2014_01
Patent number
US08637498B2

Reaction notes

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