4-Nitrobenzoic Acid → HCID 86657839, compound

HRID 1972092Notes

Reaction equation

HRID 1972092 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@H:10]([OH:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:45]([C:48]1[CH:56]=[CH:55][C:51]([C:52](O)=[O:53])=[CH:50][CH:49]=1)([O-:47])=[O:46].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[C@H:10]([O:25][C:52](=[O:53])[C:51]2[CH:50]=[CH:49][C:48]([N+:45]([O-:47])=[O:46])=[CH:56][CH:55]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58745550(3R,4R)-rel-tert-Butyl 4-(((benzyloxy)carbonyl)amino)-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 86657839HCID 86657839, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (±)-trans-4-benzyloxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1 mmol, 0.35 g), triphenylphosphine (1.5 mmol, 0.393 g) and p-nitrobenzoic acid (1.5 mmol, 0.25 g) in anhydrous THF (6 mL) at −60° C. was added DIAD drop-wise over 5 min period. After completion of addition, the reaction mixture was stirred for 4 h during which period the reaction mixture was slowly let attain room temperature. The reaction mixture was diluted with ether (100 mL) and washed with saturated sodium bicarbonate solution (2×50 mL). The organic layer was dried, filtered and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography by eluting with 30% ethyl acetate in hexanes to get (±)-cis-4-benzyloxycarbonylamino-3-(4-nitro-benzoyloxy)-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. additionAfter completion of addition
  2. customwas slowly let attain room temperature
  3. washwashed with saturated sodium bicarbonate solution (2×50 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash silica gel column chromatography
  8. washby eluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a9ac8d4e05ab413cab999bfe30d3e81b
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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