4-Nitrobenzoic Acid → HCID 58437735, compound

HRID 2170776Notes

Reaction equation

HRID 2170776 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-f4e5270f5d594318a253d5af4fe0dc1a
Source dataset
uspto-grants-2015_06
Patent number
US09051279B2

Reaction notes

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