HCID 6463212, compound → HCID 18753534, compound

HRID 1838411Notes

Reaction equation

HRID 1838411 reaction equation
CN(S(C1C=CC(OC2C=CC=CC=2)=CC=1)(=O)=O)CC(O)=O.C([O:30][CH2:31][N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](=[O:42])[N:34]([CH2:43][CH2:44][CH:45]([C:64]([OH:66])=[O:65])[N:46]([CH3:63])[S:47]([C:50]2[CH:55]=[CH:54][C:53]([O:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[CH:52][CH:51]=2)(=[O:49])=[O:48])[C:33]1=[O:67])C1C=CC=CC=1>O1CCCC1.CO.[OH-].[Pd+2].[OH-]>[OH:30][CH2:31][N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](=[O:42])[N:34]([CH2:43][CH2:44][CH:45]([C:64]([OH:66])=[O:65])[N:46]([CH3:63])[S:47]([C:50]2[CH:55]=[CH:54][C:53]([O:56][C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)=[CH:52][CH:51]=2)(=[O:49])=[O:48])[C:33]1=[O:67]

Participants

6

Reactant 2

HCID 6463212HCID 6463212, compoundHCID 18753587HCID 18753587, compound

Product 1

HCID 18753534HCID 18753534, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (±)-2-[2-(1-benzyloxymethylquinazolin-2,4-dione-3-yl)ethyl)]-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine (1.89 g, 3.0 mmol), the product of (4) above, in tetrahydrofuran (30 ml) was added to a suspension of palladium hydroxide (20%, containing 50% water, 0.42 g, 0.30 mmol) in methanol (30 ml). The mixture was stirred vigorously under a hydrogen atmosphere at 50° C. for 2 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to afford (±)-2-[2-(1-hydroxymethylquinazolin-2,4-dione-3-yl)ethyl]-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine (1.62 g) as a colorless amorphous solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-76f90298b5874c52b46dec5ff9faee93
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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