N'-Hydroxycyclopropanecarboximidamide → HCID 58002131, compound

HRID 1643169Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:11][CH:10]([C:24]([OH:26])=O)[CH2:9]1)=[O:7].O[N:28]=[C:29]([CH:31]1[CH2:33][CH2:32]1)[NH2:30]>>[CH:31]1([C:29]2[N:30]=[C:24]([CH:10]3[CH2:11][CH:12]([C:14]4[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=4)[CH2:13][N:8]([C:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:7])[CH2:9]3)[O:26][N:28]=2)[CH2:33][CH2:32]1

Participants

Reactant 2

HCID 2794666N'-Hydroxycyclopropanecarboximidamide

HCID 58002436HCID 58002436, compound

Product 1

HCID 58002131HCID 58002131, compoundYield 38.8%

Procedure

100 mg (0.267 mmol) of the compound from Example 105A and 54 mg (0.534 mmol) of N′-hydroxycyclopropanecarboximidamide were reacted according to the General Method 2. Diastereomer separation of 64 mg of the cis/trans isomer mixture according to Method 14C gave 45.4 mg of the title compound and 5.5 mg of the trans isomer.

Workup

customDiastereomer separation of 64 mg of the cis/trans isomer mixture

Sources & evidence

ORD record: ord-b20ec1a7c6984126be0a9d06046785a0
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

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