Tacrolimus-13C,D2 → HCID 57194283, compound

HRID 973705Notes

Reaction equation

HRID 973705 reaction equation
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:8]([CH3:55])[CH:7]([OH:56])[CH2:6][C:5]1=[O:57])[CH:2]=[CH2:3].N1C(C)=CC=C[C:59]=1[CH3:65].FC(F)(F)S(O[Si](C(C)C)(C(C)C)C(C)C)(=O)=[O:69]>C(Cl)Cl>[C:59]([O:40][CH:19]1[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:8]([CH3:55])[CH:7]([OH:56])[CH2:6][C:5](=[O:57])[CH:4]([CH2:1][CH:2]=[CH2:3])[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]1([OH:39])[CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])(=[O:69])[CH3:65]

Participants

5

Reactant 3

HCID 5372Tacrolimus-13C,D2HCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Product 1

HCID 57194283HCID 57194283, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (0° C.) of 17-allyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10,16-tetraone (120 mg) in dry methylene chloride (15 ml) is added 2,6-lutidine (64.3 mg) followed by triisopropylsilyl trifluoromethanesulfonate (184 mg). Reaction temperature is raised to r.t. and stirred overnight under nitrogen atmosphere. The reaction is quenched with 10 ml of water and extracted with ethyl acetate. Organic layer is washed (water, sat'd NaHCO3, sat'd NaCl) and dried (anhydrous MgSO4). Removal of solvent followed by chromatography on silica gel (70% hexane/ethyl acetate) gives the title compound.

Workup

  1. customReaction temperature
  2. customThe reaction is quenched with 10 ml of water
  3. extractionextracted with ethyl acetate
  4. washOrganic layer is washed (water, sat'd NaHCO3, sat'd NaCl)
  5. dry with materialdried (anhydrous MgSO4)
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-abe33ee27beb47f98c8dc745bed6ef7e
Source dataset
uspto-grants-1991_11
Patent number
US05064835

Reaction notes

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