Bicarbonate Ion → HCID 86746969, compound

HRID 1587758Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:19][C@H:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][C:11]=3CN2CCOCC2)[N:7]([C:28]#[N:29])[CH2:6]1)=[O:4].C(N(CC)CC)C.Cl[O:38][C:39](C)(C)C.C(=O)(O)[O-]>O1CCCC1.C(OCC)(=O)C>[C:28]([N:7]1[C@H:8]2[C@@H:18]([C:17]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:20]=3[C:10]([CH2:9]2)=[C:11]([CH:39]=[O:38])[NH:12]4)[CH2:19][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1)#[N:29]

Participants

Conditions

Temperature: -40 °C

Procedure

7.89 g of 6-cyano-2-morpholinomethyl-8beta-ergoline-carboxylic acid methyl ester (20 mmol) is dissolved in 400 ml of anhydrous tetrahydrofuran, the solution is cooled to -40° C., mixed with 4 ml of triethylamine and then the solution of 3.0 ml of tert-butyl hypochloride (25 mmol) in 60 ml of anhydrous tetrahydrofuran is instilled. After 10 minutes of stirring, another 1 ml of tert-butylhypochlorite is added, stirred for 5 minutes and the solution is poured on ice. The mixture is made alkaline with bicarbonate solution and shaken with ethyl acetate. The organic phases are dried, the solvent is evaporated and the residue is crystallized from the diisopropylether, the yield is quantitative [α]D =+42.7° (0.5% in chloroform).

Workup

stirringstirred for 5 minutes
additionthe solution is poured on ice
customThe organic phases are dried
customthe solvent is evaporated
customthe residue is crystallized from the diisopropylether
customis quantitative [α]D =+42.7° (0.5% in chloroform)

Sources & evidence

ORD record: ord-5d153003905b490cb1d28c08267739d8
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05219862

Reaction notes

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