Hydrochloric Acid → HCID 86731829, compound

HRID 1846980Notes

Reaction equation

HRID 1846980 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]([S:17]([CH2:20][C@@H:21]([N:25]1[C@H:30]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([F:38])[CH:32]=2)[C@@H:29]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=2)[CH2:28][C@@:27]([CH2:47][C:48](O)=[O:49])([CH3:46])[C:26]1=[O:51])[CH:22]1[CH2:24][CH2:23]1)(=[O:19])=[O:18])([CH3:16])([CH3:15])[CH3:14].[NH2:52][C:53]1[CH:62]=[CH:61][C:56]([C:57]([O:59][CH3:60])=[O:58])=[C:55]([O:63][CH3:64])[CH:54]=1.Cl>N1C=CC=CC=1.CCOCC>[C:13]([S:17]([CH2:20][C@@H:21]([N:25]1[C@H:30]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([F:38])[CH:32]=2)[C@@H:29]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=2)[CH2:28][C@@:27]([CH2:47][C:48]([NH:52][C:53]2[CH:62]=[CH:61][C:56]([C:57]([O:59][CH3:60])=[O:58])=[C:55]([O:63][CH3:64])[CH:54]=2)=[O:49])([CH3:46])[C:26]1=[O:51])[CH:22]1[CH2:23][CH2:24]1)(=[O:19])=[O:18])([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 168705Methyl 4-amino-o-anisateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86731830HCID 86731830, compound

Product 1

HCID 86731829HCID 86731829, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC, 76 g, 398 mmol) was added to a mixture of 2-((3R,5R,6S)-1-((S)-2-(tert-butylsulfonyl)-1-cyclopropylethyl)-6-(4-chloro-3-fluorophenyl)-5-(3-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetic acid (79.4 g, 133 mmol, Example 4, Step J) and methyl 4-amino-2-methoxybenzoate (26.4 g, 146 mmol) in pyridine (332 mL) at 3° C. The mixture was allowed to warm to room temperature and was stirred at room temperature for 16 hours. The reaction mixture was cooled to 0° C. and added to an ice-cold solution of 1 M hydrochloric acid (1 L). Ether (1 L) was added and the layers were agitated and then separated. The organic layer was washed with 1 M hydrochloric acid (6×500 mL), saturated aqueous sodium bicarbonate (500 mL), brine (500 mL), dried over magnesium sulfate, filtered and concentrated under a vacuum to provide an off-white foam.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe layers were agitated
  3. customseparated
  4. washThe organic layer was washed with 1 M hydrochloric acid (6×500 mL), saturated aqueous sodium bicarbonate (500 mL), brine (500 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under a vacuum
  8. customto provide an off-white foam

Sources & evidence

ORD record
ord-a544d5f8687f414d8d53f796a8e99aa1
Source dataset
uspto-grants-2015_02
Patent number
US08952036B2

Reaction notes

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