Hydrochloric Acid → HCID 23668431, compound

HRID 1799703Notes

Reaction equation

HRID 1799703 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[N:7]=[CH:8][S:9][C:10]=1/[CH:11]=[CH:12]\[S:13][C:14]1[C@H:15]([CH3:45])[C@@H:16]2[C@@H:33]([C@H:34]([O:36][Si](CC)(CC)CC)[CH3:35])[C:32](=[O:44])[N:17]2[C:18]=1[C:19]([O:21]CC1C=CC([N+]([O-])=O)=CC=1)=[O:20].Cl.O.C(=O)(O)[O-].[Na+:52].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>C1COCC1.O.[Pd]>[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[N:7]=[CH:8][S:9][C:10]=1/[CH:11]=[CH:12]\[S:13][C:14]1[C@H:15]([CH3:45])[C@@H:16]2[C@@H:33]([C@H:34]([OH:36])[CH3:35])[C:32](=[O:44])[N:17]2[C:18]=1[C:19]([O-:21])=[O:20].[Na+:52]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24243Trisodium PhosphateHCID 69467537HCID 69467537, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 23668431HCID 23668431, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl (1R,5S,6S)-2-[[(Z)-2-[4-(2-hydroxyethoxy)methylthiazol-5-yl]ethen-1-yl]thio]-1-methyl-6-((1R)-1-triethylsilyloxy ethyl)-1-carbapen-2-em-3-carboxylate (3.82 g) was dissolved in 170 ml of THF and 70 ml of water. 1 N aqueous hydrochloric acid (2.8 ml) was added to the solution, and the mixture was stirred at room temperature for 50 min. The reaction solution was adjusted to pH 3.0 by the addition of saturated sodium bicarbonate water. A 1/15 M sodium phosphate buffer solution (pH 6.8) (170 ml) and 3.10 g of 10% Pd—C (hydrous, water content 53%) were added thereto, and the mixture was stirred under a hydrogen atmosphere for 1.5 hr. 10% Pd—C was removed by filtration and was washed with water, and the filtrate was adjusted to pH 7.0 by the addition of saturated sodium bicarbonate water, followed by washing with 300 ml of ethyl acetate. The aqueous layer was concentrated to about 20 ml, and the residue was purified by column chromatography on Cosmosil 40C18-PREP (5% methanol-water) to give 1.91 g of the title compound.

Workup

  1. stirringthe mixture was stirred under a hydrogen atmosphere for 1.5 hr
  2. custom10% Pd—C was removed by filtration
  3. washwas washed with water
  4. additionthe filtrate was adjusted to pH 7.0 by the addition of saturated sodium bicarbonate water
  5. washby washing with 300 ml of ethyl acetate
  6. concentrationThe aqueous layer was concentrated to about 20 ml
  7. customthe residue was purified by column chromatography on Cosmosil 40C18-PREP (5% methanol-water)

Sources & evidence

ORD record
ord-641227ecced241078c0ee1a83b4dc868
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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