N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → HCID 53854983, compound

HRID 989645Notes

Reaction equation

HRID 989645 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH:7]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:8](=[O:12])[N:9]([CH3:11])[CH2:10][C:4]=2[CH:3]=1.[C:20]([NH:27][CH2:28][CH2:29][C:30](O)=[O:31])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>>[C:23]([O:22][C:20]([NH:27][CH2:28][CH2:29][C:30]([NH:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH:7]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:8](=[O:12])[N:9]([CH3:11])[CH2:10][C:4]=2[CH:3]=1)=[O:31])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 53747305HCID 53747305, compound

Product 1

HCID 53854983HCID 53854983, compoundYield 87%

Procedure

Methyl (±)-8-amino-2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate was coupled with Boc-β-alanine according to the procedure of Example 5(b). Purification by chromatography on silica gel gave the title compound (87%) as a light yellow foam: 1H NMR (CDCl3) δ8.20 (br s, 1H), 7.48 (s, 1H), 7.20 (d, J=8.3 Hz, 1H), 7.04 (d, J=8.3 Hz, 1H), 5.27 (d, J=16.6 Hz, 1H), 3.92 (m, 3H), 3.80 (d, J=16.6 Hz, 1H), 3.70 (s, 3H), 3.01 (s, 3H), 2.90 (m, 5H), 2.48 (dd, J=16.8, 5.5 Hz, 1H), 1.48 (s, 9H).

Workup

  1. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-4df78e0b53e0411d90e35fbf9997f0b0
Source dataset
uspto-grants-2002_10
Patent number
US06458784B1

Reaction notes

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