tert-Butyl methyl ether → HCID 67203600, compound

HRID 547960Notes

Reaction equation

HRID 547960 reaction equation
C(OC([N:8]1[C:22]2[C:23]3[C:10]([CH2:11][C@@H:12]4[C@@H:17]([C:18]=3[CH:19]=[CH:20][CH:21]=2)[CH2:16][C@@H:15]([C:24]([OH:26])=[O:25])[CH2:14][N:13]4C(OC(C)(C)C)=O)=[CH:9]1)=O)(C)(C)C.S(Cl)([Cl:36])=O.[C:38](OC)(C)(C)C>CO>[ClH:36].[C@@H:15]1([C:24]([O:26][CH3:38])=[O:25])[CH2:16][C@H:17]2[C@@H:12]([CH2:11][C:10]3[C:23]4[C:22](=[CH:21][CH:20]=[CH:19][C:18]2=4)[NH:8][CH:9]=3)[NH:13][CH2:14]1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24386Thionyl ChlorideHCID 59841562HCID 59841562, compound

Product 1

HCID 67203600HCID 67203600, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
52.5 °C

Procedure

To a mixture of 1,6-di-(tert-butoxycarbonyl)-ergoline-8β-carboxylic acid (300 g) in methanol (1.2 L) is slowly added thionyl chloride (94 g). The mixture is slowly heated to 50-55° C. and stirred until reaction completion (ca. 4-5 h). The resulted suspension is cooled to room temperature and to it is added methyl t-butyl ether (600 mL) and heptanes (1.8 L). The suspension is further cooled to 0-5° C. Filtered and washed with methyl t-butyl ether. The isolated solid is dried to give methyl ergoline-8β-carboxylate hydrochloride (190.5 g) in 94.5% yield.

Workup

  1. temperatureThe resulted suspension is cooled to room temperature and to it
  2. temperatureThe suspension is further cooled to 0-5° C
  3. filtrationFiltered
  4. washwashed with methyl t-butyl ether
  5. customThe isolated solid is dried

Sources & evidence

ORD record
ord-cb16ef7756ee4185998ac95f70526a72
Source dataset
uspto-grants-2011_05
Patent number
US07939665B2

Reaction notes

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