Hydrochloric Acid → HCID 178454259, compound

HRID 1418622Notes

Reaction equation

HRID 1418622 reaction equation
[CH3:1][C:2]([CH3:40])([O:4][C:5]([NH:7][C:8]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=[O:39])[NH:25][CH:26]([C:35]([O:37]C)=[O:36])[O:27][Si:28]([CH3:34])([CH3:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[N:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:6])[CH3:3].[OH-].[Na+].O.Cl>COCCOC.ClCCl>[CH3:15][C:13]([CH3:16])([O:12][C:10]([NH:9][C:8]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=[O:39])[NH:25][CH:26]([C:35]([OH:37])=[O:36])[O:27][Si:28]([CH3:33])([CH3:34])[C:29]([CH3:31])([CH3:30])[CH3:32])=[N:7][C:5]([O:4][C:2]([CH3:1])([CH3:3])[CH3:40])=[O:6])=[O:11])[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178501666HCID 178501666, compound

Product 1

HCID 178454259HCID 178454259, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.73 g (2.94.10-3 mol) of 3-[[(1,1-dimethylethoxy)carbonyl]amino]-13-(methoxycarbonyl)-15,15,16,16-tetramethyl-11-oxo-14-oxa-2,4,12-triaza-15-silaheptadec-2-enoic acid, 1,1-dimethylethyl ester are dissolved in 4 ml of 1,2-dimethoxyethane, and 4 ml of molar aqueous sodium hydroxide solution are added. The reaction mixture is stirred for 10 minutes at room temperature, 20 ml of water and 20 ml of dichloromethane are then added and the mixture is acidified to pH 2 with 1N hydrochloric acid, with thorough stirring. After separation of the organic phase, the aqueous phase is extracted with 3 times 25 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate and then concentrated under reduced pressure to give 1.68 g of the expected product in the form of a colorless oil (quantitative yield).

Workup

  1. customAfter separation of the organic phase
  2. extractionthe aqueous phase is extracted with 3 times 25 ml of dichloromethane
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c64192ca60fa48bfb496d76ea523868e
Source dataset
uspto-grants-1999_03
Patent number
US05883132

Reaction notes

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