4-Nitrobenzoic Acid → HCID 58437735, compound

HRID 2092398Notes

Reaction equation

HRID 2092398 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH:9]1[CH2:12][CH:11]([OH:13])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[N+:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)([O-:17])=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([NH:7][CH2:8][CH:9]1[CH2:10][CH:11]([O:13][C:22](=[O:23])[C:21]2[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:26][CH:25]=2)[CH2:12]1)=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 22408693tert-Butyl [(3-hydroxycyclobutyl)methyl]carbamate

Product 1

HCID 58437735HCID 58437735, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of (3-Hydroxy-cyclobutylmethyl)-carbamic acid tert-butyl ester (6.98 g, 34.7 mmol), 4-nitrobenzoic acid (11.59 g, 69.4 mmol) and triphenylphosphine (18.19 g, 69.4 mmol) in THF (1 L) was added a solution of DIAD (14.76 g, 69.4 mmol) in THF (10 mL). After removal of the ice bath, the mixture was stirred at RT for 15 h. The mixture was concentrated to dryness and the oily residue was purified normal phase column chromatography (elution with DCM) yielding the title intermediate as a yellow solid (9.89 g, 22.58 mmol, 65%), HPLC: FtRet=1.354; LC-MS: m/z 368.3 [M+NH4]+.

Workup

  1. customAfter removal of the ice bath
  2. concentrationThe mixture was concentrated to dryness
  3. customthe oily residue was purified normal
  4. washphase column chromatography (elution with DCM)

Sources & evidence

ORD record
ord-8bf30cea9be0412c8ba1c5690513ff09
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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