Chloroacetyl chloride → tert-Butyl (2-{(chloroacetyl)[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate

HRID 1466024Notes

Reaction equation

HRID 1466024 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])#[N:2].CCN(CC)CC.[Cl:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[Cl:32][CH2:33][C:34]([N:14]([CH2:13][CH:8]1[C:9]2[C:4](=[C:3]([C:1]#[N:2])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1)[CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:35]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 131732671Tert-butyl (2-{[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate

Product 1

HCID 131732672tert-Butyl (2-{(chloroacetyl)[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-Butyl (2-{[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate (0.20 g, 0.61 mmol) in DCM (5 mL) was added Et3N (74 mg, 7.2 mmol), followed by chloro-acetyl chloride (81 mg, 7.2 mmol). The reaction mixture was stirred overnight. The product was purified by prep-TLC (Pet Ether:EtOAc=1:1) to give the title product. MS m/z: 406 [M+1]+.

Workup

  1. customThe product was purified by prep-TLC (Pet Ether:EtOAc=1:1)

Sources & evidence

ORD record
ord-13eed066bba845549232952062d529da
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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