Glycine methyl ester → Methyl ({2-[(tert-butoxycarbonyl)(7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethyl}amino)acetate

HRID 1466054Notes

Reaction equation

HRID 1466054 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:21][CH:22]=O)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[NH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[C:16]([O:15][C:14]([N:13]([CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:10]1)[CH2:21][CH2:22][NH:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[O:20])([CH3:17])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 69221Glycine methyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 131732680tert-Butyl (7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)(2-oxoethyl)carbamate

Product 1

HCID 131732681Methyl ({2-[(tert-butoxycarbonyl)(7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethyl}amino)acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-Butyl (7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)(2-oxoethyl)carbamate (260 mg, 0.83 mmol) in 10 mL of anhydrous DCM was added Gly-OMe (150 mg, 1.7 mmol), 2 drops of HOAc and NaBH(OAc)3 (180 mg, 0.83 mmol) and the mixture was stirred at ambient temperature overnight. Then DCM was added, and the mixture was washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to the title compound. MS m/z: 388 [M+1]+.

Workup

  1. washthe mixture was washed with brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC to the title compound

Sources & evidence

ORD record
ord-8de4aeb3eb9543c49cb7d36832734b9e
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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