4-Methylmorpholine → HCID 178462203, compound

HRID 2286612Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)C(C)(C)C.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:40]=[C:39]([OH:41])[C:38]([C:42]([OH:44])=[O:43])=[CH:37][N:36]=2)=[CH:31][CH:30]=1.C(N(CC)CC)C>C(#N)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[N:40]=[C:39]([OH:41])[C:38]([C:42]([OH:44])=[O:43])=[CH:37][N:36]=2)=[CH:33][CH:34]=1)=[O:13])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 5.67 g (30 mmol) of N-t-butoxycarbonyl-L-alanine in 75 ml of acetonitrile is stirred at 0° and 6.36 g (63 mmol) of N-methylmorpholine is added and the mixture cooled to -20° C. Next 3.62 g (30 mmol) of pivaloyl chloride is added and the mixture stirred at -15° C. for 1.5 hrs and a solution cooled to -10° C., containing 3.46 g (15 mmol) of 2-(4-aminophenyl) 4-hydroxy-5-pyrimidine carboxylic acid, 75 ml of acetonitrile, and 4.17 ml (30 mmol) of triethylamine is added. After stirring for 2 hrs at -10° C. the mixture is then kept at room temperature for 18 hrs. The solution is evaporated to near dryness in vacuo and treated with 200 ml of water. The pH is adjusted to 2.8 with citric acid and the product filtered, washed with water and ether, and dried to give 5.8 g of 2-[4-(N-t-butoxycarbonyl-L-alanylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid. [α]D23 -28.5° (cl, pH 7).

Workup

temperaturea solution cooled to -10° C.
additionis added
stirringAfter stirring for 2 hrs at -10° C. the mixture
waitis then kept at room temperature for 18 hrs
customThe solution is evaporated
additiontreated with 200 ml of water
filtrationthe product filtered
washwashed with water and ether
customdried

Sources & evidence

ORD record: ord-fc5893368ee74b5b86807a6928d32ce1
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04267180

Reaction notes

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