Triethylamine → Ethyl 3-(4-(3,3-dimethylcyclobutanecarbonyl)benzamido)propanoate

HRID 537485Notes

Reaction equation

HRID 537485 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:5][CH:4]([C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[O:7])[CH2:3]1.Cl.[NH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].O.N1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C>O1CCCC1>[CH3:17][C:2]1([CH3:1])[CH2:3][CH:4]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:14])=[CH:15][CH:16]=2)=[O:7])[CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 681574694-(3,3-Dimethylcyclobutanecarbonyl)benzoic acid

Product 1

HCID 68156595Ethyl 3-(4-(3,3-dimethylcyclobutanecarbonyl)benzamido)propanoateYield 63.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (138 mL) was added to a vial containing 4-(3,3-dimethylcyclobutanecarbonyl)benzoic acid (3.20 g, 14.0 mmol), ethyl 3-aminopropanoate hydrochloride (3.17 g, 20.7 mmol) and 1,2,3-benzotriazol-1-ol monohydrate (2.22 g, 14.5 mmol). Triethylamine (9.11 mL, 4.75 mmol) was then added. The reaction was stirred for 16 h, and was then concentrated. Purification by column chromatography (0-35% ethyl acetate in heptane) afforded impure ethyl 3-(4-(3,3-dimethylcyclobutanecarbonyl)benzamido)propanoate (4.22 g, approximately 8.90 mmol pure) as an oil. MS (M+1) 332.2.

Workup

  1. concentrationwas then concentrated
  2. customPurification by column chromatography (0-35% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-ef6988d6f73f4122b6094c4e877b25ba
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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