Acetic Acid → HCID 66756970, compound

HRID 1642633Notes

Reaction equation

HRID 1642633 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:33][C:34]([OH:36])=[O:35].[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:38].[Na+]>C(#N)C>[CH2:37]([O:35][C:34](=[O:36])[CH2:33][NH:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:38]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 66756490HCID 66756490, compound

Product 1

HCID 66756970HCID 66756970, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl glyoxlate is added to a solution of 2-(4-amino-3-benzyloxybenzyl)-6-benzyloxybenzonitrile (0.281 g, 0.668 mmol), ACN (3 mL) and AcOH (1.5 mL) under N2. The mixture is stirred at ambient temperature for 2 h. The reaction is cooled in an ice bath and a slurry of sodium triacetoxyborohydride (0.284 g, 1.34 mmol) and ACN (1.5 mL) is added dropwise. Upon consumption of the starting material by LC/MS, the reaction is concentrated and the residue quenched with saturated NaHCO3 (2×10 mL). The mixture is extracted with DCM (40 mL) and the organics dried over Na2CO3. Evaporation affords [2-benzyloxy-4-(3-benzyloxy-2-cyanobenzyl)-phenylamino]-acetic acid ethyl ester as a green oil: MS (M+H)+=507.

Workup

  1. temperatureThe reaction is cooled in an ice bath
  2. customUpon consumption of the starting material by LC/MS
  3. concentrationthe reaction is concentrated
  4. customthe residue quenched with saturated NaHCO3 (2×10 mL)
  5. extractionThe mixture is extracted with DCM (40 mL)
  6. dry with materialthe organics dried over Na2CO3
  7. customEvaporation

Sources & evidence

ORD record
ord-c083ae6a98f245f594e1094e38e9ed54
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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