Ethyl Acetate → HCID 86757480, compound

HRID 379660Notes

Reaction equation

HRID 379660 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[CH:5]=[O:6].[C:12]([O:16][C:17](N(CC(O)=O)C)=[O:18])([CH3:15])([CH3:14])[CH3:13].Cl.[CH3:26][N:27](C)[CH2:28][CH2:29]CN=C=NCC.C(OCC)(=[O:39])C>CN(C1C=CN=CC=1)C.ClCCl>[C:12]([O:16][C:17]([CH2:26][NH:27][CH2:28][C:29]([O:10][C:9]1[C:8]([CH3:11])=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[CH3:1])=[O:39])=[O:18])([CH3:13])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86757480HCID 86757480, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.35 g of 3,5-dimethyl-4-hydroxybenzaldehyde, 1.73 g of N-(tert-butoxycarbonyl)sarcosine and 0.2 g of 4-(N,N-dimethylamino)pyridine in 20 ml of dichloromethane was added 1.9 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and stirring was continued for 2.5 h at room temperature. The mixture was diluted with ethyl acetate and was washed with 0.25N HCl. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain 4-(tert-butoxycarbonylmethylamino)acetoxy-3,5-dimethylbenzaldehyde (2.9 g) as a yellow oil.

Workup

  1. washwas washed with 0.25N HCl
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7d0fdd23981441b6a380a7e9ab75ee1b
Source dataset
uspto-grants-2001_10
Patent number
US06300353B1

Reaction notes

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