Triethylamine → HCID 178510905, compound

HRID 1005345Notes

Reaction equation

HRID 1005345 reaction equation
C[O:2][C:3]([C:5]([C@H:27]1[CH2:30][C@@H:29]([C:31]([O:33]C)=[O:32])[CH2:28]1)([CH2:9][CH2:10][CH:11]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:18](=[O:26])(=[O:25])[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)C(O)=O)=[O:4].C([N:37](CC)CC)C>C1(C)C=CC=CC=1>[NH2:37][C:5]([C@H:27]1[CH2:30][C@@H:29]([C:31]([OH:33])=[O:32])[CH2:28]1)([CH2:9][CH2:10][CH:11]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:18](=[O:26])(=[O:25])[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:3]([OH:2])=[O:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 178500084HCID 178500084, compound

Product 1

HCID 178510905HCID 178510905, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of cis-2-methoxycarbonyl-2-(3-methoxy carbonylcyclobutyl)-4-(10,10-dioxido-9-thioxanthyl)butanoic acid (0.87 g, 1.79 mmol), triethylamine (0.19 g, 1.88 mmol) and diphenyl phosphonic azide (0.33 g, 1.88 mmol) in toluene (30 ml) were heated at 75° C. and worked up following the procedure described in Example 17(iii). The crude product was purified by chromatography on flash silica eluting with diethyl ether-hexane (7:3) to give a colourless oil and then crystallised from diethyl ether to give the title compound.

Workup

  1. customThe crude product was purified by chromatography on flash silica eluting with diethyl ether-hexane (7:3)
  2. customto give a colourless oil
  3. customcrystallised from diethyl ether

Sources & evidence

ORD record
ord-318c4d36ab094c71b2a10ac1689b8b80
Source dataset
uspto-grants-2000_04
Patent number
US06054448

Reaction notes

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