Hydrochloric Acid → HCID 6999427, compound

HRID 2248037Notes

Reaction equation

[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].Cl.[NH2:17][C@H:18]([C:20]([O:22][CH3:23])=[O:21])[CH3:19].C(N(CC)CC)C.C(OC(Cl)=O)C>C1COCC1>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([NH:17][C@H:18]([C:20]([O:22][CH3:23])=[O:21])[CH3:19])=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

Conditions

Temperature: -15 °C

Procedure

The condensation of BOC-Val-OH with HCl. Ala-OMe was carried out by a mixed anhydride method. 12 g (0.055 mol) of BOC-Val-OH was dissolved in 40 ml of dry THF and 5.6 g (0.055 mol) of triethylamine and 6.6 g (0.06 mol) of chloroformic acid ethyl ester was added to the solution after cooling to -15° C. After 10 minutes at low temperature 7.7 g (0.055 mol) of HCl.Ala-OMe and 5.6 g (0.055 mol) of triethylamine were slowly added to the mixture at -15° C. The reaction mixture was stirred for a further 16 hours at room temperature. The THF was evaporated and the product extracted with ethyl acetate. Recrystalization from ether gave 8.1 g of analytically pure BOC-Val-Ala-OMe, m.p. 138°-148° C.

Workup

customThe THF was evaporated
extractionthe product extracted with ethyl acetate
customRecrystalization from ether

Sources & evidence

ORD record: ord-95da1ae91119426db6daa673fa6372ae
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05037883

Reaction notes

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