Hydrochloric Acid → HCID 58010639, compound

HRID 2062234Notes

Reaction equation

HRID 2062234 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:4](=[O:12])O1.Cl.[Na+].[Cl-].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:38]1([C:44]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C(N(CC)CC)C>C1COCC1>[CH2:47]([O:46][C:44]([N:38]1[CH2:43][CH2:42][N:41]([C:4](=[O:12])[C@H:5]([OH:6])[CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH2:40][CH2:39]1)=[O:45])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 643495Benzyl piperazine-1-carboxylateHCID 10655203Methyl (R)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-YL)acetate

Product 1

HCID 58010639HCID 58010639, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetate (17.1 g, 90.9 mmol) was stirred in a 1:1 mixture of THF: 1 M HCl (200 mL) for 1 h at room temperature. After addition of NaCl to nearly saturate the aqueous layer, the mixture was extracted with EtOAc, and the extracts were dried over Na2SO4 and concentrated. To the resulting oil dissolved in dry DMF (500 mL) was added HOBt (13.5 g, 100 mmol) and EDCI (19.2 g, 100 mmol). After stirring for 5 min, benzyl piperazine-1-carboxylate (19.3 mL, 100 mmol) and triethylamine (13.9 mL, 100 mmol) were added to the reaction mixture, which was left stirring at room temperature overnight. Purification via silica gel chromatography using 0-10% MeOH/CH2Cl2 provided a colorless oil 4-((R)-2-hydroxy-3-methoxycarbonyl-propionyl)-piperazine-1-carboxylic acid benzyl ester (6.71 g, 21%). LC/MS: m/z 351.5 (M+H)+ at 2.67 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. concentrationto nearly saturate the aqueous layer
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialthe extracts were dried over Na2SO4
  4. concentrationconcentrated
  5. dissolutionTo the resulting oil dissolved in dry DMF (500 mL)
  6. waitwas left
  7. stirringstirring at room temperature overnight
  8. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-02b1658db3d04907a009aae1a2de680c
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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