Water → HCID 23520109, compound

HRID 1007672Notes

Reaction equation

HRID 1007672 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][C@H:10]([NH:74]C(OCC1C=CC=CC=1)=O)[C:11]([NH:13][CH:14]([CH2:65][CH2:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[C:15]([NH:17][CH2:18][CH2:19][NH:20][C:21]([CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([S:34]([NH:37][C@@H:38]([CH2:42][NH:43][C:44]([C:46]2[CH:47]=[C:48]3[C:52](=[CH:53][CH:54]=2)[N:51]([CH2:55][CH2:56][CH2:57][NH:58][C:59]2[NH:60][CH:61]=[CH:62][N:63]=2)[N:50]=[CH:49]3)=[O:45])[C:39]([OH:41])=[O:40])(=[O:36])=[O:35])=[C:29]([CH3:64])[CH:28]=1)=[O:22])=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O>CO.[Pd].O.C(#N)C>[NH2:74][C@@H:10]([CH2:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:11]([NH:13][CH:14]([CH2:65][CH2:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[C:15]([NH:17][CH2:18][CH2:19][NH:20][C:21]([CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]([CH3:64])[C:30]([S:34]([NH:37][C@@H:38]([CH2:42][NH:43][C:44]([C:46]2[CH:47]=[C:48]3[C:52](=[CH:53][CH:54]=2)[N:51]([CH2:55][CH2:56][CH2:57][NH:58][C:59]2[NH:60][CH:61]=[CH:62][N:63]=2)[N:50]=[CH:49]3)=[O:45])[C:39]([OH:41])=[O:40])(=[O:35])=[O:36])=[C:31]([CH3:33])[CH:32]=1)=[O:22])=[O:16])=[O:12]

Participants

6

Reactant 2

HCID 962Water2×HCID 60111032HCID 60111032, compound

Product 1

HCID 23520109HCID 23520109, compoundYield 114.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The product of step B (25 mg, 24 umol) in methanol (3 mL) was added to 10% palladium on carbon (14 mg) in methanol (3 mL) under nitrogen in a Parr bottle. It was hydrogenolyzed at 50 psi for 180 min, filtered through Celite, rinsed with methanol, and concentrated to afford a viscous oil. This was redissolved in 1:1 water/acetonitrile containing 0.1% TFA (nmL) and lyophilized (1:1 acetontrile/water/0.1% TFA) to afford the product as a white powder (29 mg, 100% yield) which analyzes for 2 equal peaks by HPLC (4.6×150 mm Zorbax C-18, 1 mL/min; Water/90% acetonitrile/0.1% trifluoroacetic acid, 2-100% B over 14 min) Rt=9.78 and 10.14 minutes. LRMS (ES): 1054.5 ([M+H]+, 10%) 527.8 ([M+2H]+2, 100%); identical for each peak. This was not further purified but taken into the next step as a mixture of two diastereomers.

Workup

  1. filtrationfiltered through Celite
  2. washrinsed with methanol
  3. concentrationconcentrated
  4. customto afford a viscous oil

Sources & evidence

ORD record
ord-cd425f3425e74ebbbbdc4b660b73ae47
Source dataset
uspto-grants-2004_09
Patent number
US06794518B1

Reaction notes

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