Ammonium Hydroxide → BOC-beta-Nal-NH2

HRID 1742746Notes

Reaction equation

[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14](O)=[O:15])[CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1.[NH4+:24].[OH-]>>[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([NH2:24])=[O:15])[CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 7020908Boc-3-(2-naphthyl)-L-alanine

Product 1

HCID 12012106BOC-beta-Nal-NH2Yield 96%

Procedure

The product was prepared in 96% yield by reaction of the mixed anhydride from BOC-β-Nal-OH (682 mg, 2.17 mmol) with conc. NH4OH according to the procedure of Rzeszotarska, B., Makowski, M., and Kubica, Z. Org. Prep. Proc. Int.1984, 16:136-139. 1H-NMR (CDCl3): δ1.40 (s, 9H), 3.24 (m, 2H), 4.47 (m, 1H), 5.10 (br s, 1H), 5.37 (br s, 1H), 5.75 (br s, 1H), 7.49 (dd, J=2 Hz and 9 Hz, 1H), 7.47 (m, 2H), 7.69 (s, 1H), 7.80 (m, 3H). MS (DCl): m/e 315 (M+H)+, 259, 215.

Sources & evidence

ORD record: ord-7e4e36735f9140a1ada9f76686a87daa
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05340802

Reaction notes

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