Sodium Hydroxide → L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-

HRID 2237360Notes

Reaction equation

[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:4]([NH:6][C@H:7]([C:11]([O:13]C)=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5])[CH3:3].[OH-].[Na+]>CC(C)=O>[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:4]([NH:6][C@H:7]([C:11]([OH:13])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5])[CH3:3]

Participants

Conditions

Temperature: 23 °C

Procedure

Boc-Ala-Val-OMe 53 (1.750 g, 5.79 mmol) was stirred in 40 mL acetone. NaOH solution (8.7 mL of 2.0 M aqueous solution) was added and stirred 2 h at 23° C. Acetone was removed under reduced pressure and the resulting solution was diluted with EtOAc (20 mL). The organic fraction was washed with water (2×20 mL), dried over sodium sulfate, and concentrated in vacuo to yield 1.561 g (99%) product. 1H NMR (CDCl3, 300 MHz) δ 12.28 (br s, 1H), 7.69 (d, J=8.7 Hz, 1H), 6.98 (d, J=7.5 Hz, 1H), 4.15 (dd, J=5.4, 8.4 Hz, 1H), 4.04 (quintet, J=7.2 Hz, 1H), 3.35 (br s, 2H), 2.04 (octet, J=6.6 Hz, 1H), 1.37 (s, 9H), 1.16 (d, J=7.2 Hz, 3H), 0.87 (d, J=7.2 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 172.9, 155.1, 78.1, 56.8, 30.2, 28.2, 19.0, 18.0, 17.8.

Workup

customAcetone was removed under reduced pressure
additionthe resulting solution was diluted with EtOAc (20 mL)
washThe organic fraction was washed with water (2×20 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-419789a354724751bd8b7bae44715ede
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718600B2

Reaction notes

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