Benzoic Acid → HCID 178525738, compound

HRID 1639997Notes

Reaction equation

HRID 1639997 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([N:20]2[CH2:24][CH2:23][C@:22]3([CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])[CH2:25]3)[C:21]2=[O:40])[CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.[C:65](O)(=[O:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>>[C:65]([O:13][C@@H:14]1[CH2:15][CH2:16][C@H:17]([N:20]2[CH2:24][CH2:23][C@:22]3([CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[O:31])[CH2:25]3)[C:21]2=[O:40])[CH2:18][CH2:19]1)(=[O:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

6

Reactant 5

HCID 243Benzoic AcidHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178525119HCID 178525119, compound

Product 1

HCID 178525738HCID 178525738, compound

Procedure

Diethyl azodicarboxylate (163.0 μL, 0.001035 mol) was added to a mixture of benzyl (5S)-2-(trans-4-hydroxycyclohexyl)-1-oxo-2,7-diazaspiro[4.5]decane-7-carboxylate (200.0 mg, 0.0005175 mol, this compound was prepared by using the procedures of example 472-a, step 1), and triphenylphosphine (271.4 mg, 0.001035 mol) in tetrahydrofuran (3.0 mL, 0.037 mol) at rt. The mixture was stirred at rt for 5 minutes, then benzoic acid (66.36 mg, 0.0005434 mol) was added. After stirring for an additional 2 h, the volatiles in the mixture were removed in-vacuo and the residue was purified by flash chromatography to afford the desired product.

Workup

  1. customthis compound was prepared
  2. customat rt
  3. stirringAfter stirring for an additional 2 h
  4. customthe volatiles in the mixture were removed in-vacuo
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-177b9d21a207404a9fe1fe7b002506e4
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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