L-Phenylalanine → HCID 22806798, compound

HRID 1390274Notes

Reaction equation

[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.O1CCOCC1.[C:26](=[S:28])=O.Cl[CH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1>O>[C:31]1([CH2:30][C:26]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[S:28])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 10 °C

Procedure

8.3 G (0.05 mol) of L-phenylalanine and 13.9 ml (0.1 mol) of triethylamine were dissolved in 100 ml of water. To the solution was dropwise added 100 ml of dioxane containing 3.0 g (0.05 mol) of carbonyl sulfide at a temperature of from 5°to 10° C. in 15 minutes while cooling with ice. After stirring at a temperature of 10° C. for 15 minutes, 8.8 g (0.05 mol) of 1-(chloromethyl)-naphthalene was dropwise added to the mixture in 10 minutes and the mixture was then stirred at room temperature for 1 hour. After completion of reaction, the syrup-like substance obtained in a similar manner to that described in Example 6 was crystallized from 80 ml of ether and 100 ml of n-hexane to yield 14.8 g of white crystals.

Workup

customof from 5°to 10° C.
customin 15 minutes
temperaturewhile cooling with ice
stirringthe mixture was then stirred at room temperature for 1 hour
customAfter completion of reaction
customthe syrup-like substance obtained in a similar manner to that
customwas crystallized from 80 ml of ether and 100 ml of n-hexane

Sources & evidence

ORD record: ord-0bc3883ca8194200afec62cafa8456c3
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04138485

Reaction notes

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