Potassium Carbonate → 3-{4-[(1,4-Dioxaspiro[4.5]dec-8-ylamino)methyl]benzoylamino}propionic acid ethyl ester

HRID 1633886Notes

Reaction equation

HRID 1633886 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[O:26]1[C:30]2([CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]2)[O:29][CH2:28][CH2:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][CH2:11][NH:10][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([CH2:3][NH:2][CH:33]2[CH2:34][CH2:35][C:30]3([O:29][CH2:28][CH2:27][O:26]3)[CH2:31][CH2:32]2)=[CH:19][CH:18]=1)[CH3:17]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydrideHCID 22502125HCID 22502125, compound

Product 1

HCID 540057363-{4-[(1,4-Dioxaspiro[4.5]dec-8-ylamino)methyl]benzoylamino}propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

1.2 g Ethyl 3-(4-aminomethylbenzoylamino)propanoate hydrochloride (4.18 mmol) was mixed with 20 mL 1,2-dichloroethane and 6 mL saturated K2CO3 by vigorous stirring. The phases were separated and the aqueous phase was extracted with another 20 mL 1,2-dichloroethane. 240 μL HOAc was added to the combined 1,2-dichloroethane phase followed by 0.691 g 1,4-dioxaspiro[4.5]decan-8-one (4.42 mmol). 1.272 g NaBH(OAc)3 (6 mmol) was added and the reaction was stirred for 16 hours at 25° C. The reaction volume was reduced on a rotary evaporator to about 20 mL and then poured into a mixture of 60 mL H2O and 10 mL sat. K2CO3. The phases were separated and the aqueous phase was extracted twice with 40 mL 1,2-dichloroethane. The combined 1,2-dichloroethane fractions were dried over MgSO4 and evaporated to afford the title compound. The crude product was used in the next step without further purification.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with another 20 mL 1,2-dichloroethane
  3. addition240 μL HOAc was added to the combined 1,2-dichloroethane phase
  4. customThe reaction volume was reduced on a rotary evaporator to about 20 mL
  5. additionpoured into a mixture of 60 mL H2O and 10 mL sat. K2CO3
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted twice with 40 mL 1,2-dichloroethane
  8. dry with materialThe combined 1,2-dichloroethane fractions were dried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-7f3aafa9800a48a9b5e5a44e6b292c17
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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