Hydrochloric Acid → HCID 71041832, compound

HRID 1845977Notes

Reaction equation

HRID 1845977 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C@@:10]23[CH2:25][C@H:24]2[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:15](=[O:34])[N:14]2[CH2:35][C@H:36]([OH:38])[CH2:37][C@H:13]2[C:12](=[O:39])[NH:11]3)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.Cl[C:41]1[N:42]=[C:43]2[C:48](=[C:49]3[C:54]=1[CH:53]=[C:52]([F:55])[CH:51]=[CH:50]3)[CH:47]=[CH:46][CH:45]=[CH:44]2.CC([O-])(CC)C.[Na+].Cl>CN(C)C=O>[CH:1]1([S:4]([NH:7][C:8]([C@@:10]23[CH2:25][C@H:24]2[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])[C:15](=[O:34])[N:14]2[CH2:35][C@H:36]([O:38][C:41]4[N:42]=[C:43]5[C:48](=[C:49]6[C:54]=4[CH:53]=[C:52]([F:55])[CH:51]=[CH:50]6)[CH:47]=[CH:46][CH:45]=[CH:44]5)[CH2:37][C@H:13]2[C:12](=[O:39])[NH:11]3)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2733478Sodium 2-methylbutan-2-olateHCID 58798563HCID 58798563, compoundHCID 86673690HCID 86673690, compound

Product 1

HCID 71041832HCID 71041832, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl (2R,6S,13aS,14aR,16aS,Z)-14a-(cyclopropylsulfonylcarbamoyl)-2-hydroxy-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate (2c, 0.376 g, 0.660 mmol), 6-chloro-8-fluorophenanthridine (2b, 0.153 g, 0.660 mmol) and sodium 2-methylbutan-2-olate (0.218 g, 1.981 mmol) in dimethylformamide (6.6 mL) was stirred at room temperature for 2 h. The reaction mixture was added dropwise to 2N HCl (200 mL) and the resulting solid was collected by vacuum filtration, rinsed with water, and dried. The solid was purified by flash chromatography on silica gel, eluting with acetone/hexane, to provide the title compound (0.355 g, 70% yield) as a white solid.

Workup

  1. filtrationthe resulting solid was collected by vacuum filtration
  2. washrinsed with water
  3. customdried
  4. customThe solid was purified by flash chromatography on silica gel
  5. washeluting with acetone/hexane

Sources & evidence

ORD record
ord-341b0335139f49ddba576449cf06e90f
Source dataset
uspto-grants-2015_02
Patent number
US08951964B2

Reaction notes

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