HCID 57322588, compound → HCID 57172629, compound

HRID 248289Notes

Reaction equation

HRID 248289 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH2:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([OH:55])[CH2:5][C:4]1=[O:56])[CH3:2]>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH:50][C:10](=[O:9])[CH2:11][NH2:16])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([OH:55])[CH2:5][C:4]1=[O:56])[CH3:2]

Participants

4

Reactant 1

HCID 57322588HCID 57322588, compound

Product 1

HCID 57172629HCID 57172629, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-amino-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 in (100 mg) in dry methylene chloride (4 ml) was added 100 mg of freshly prepared BOC-L-glycine anhydride under nitrogen. After stirring at room temperature for 1.5 hours, the reaction mixture was subjected to work-up and the residue was purified on silica gel (5% MeOH/CH2Cl2) to give the 65 mg of BOC protected compound. This material (48 mg) was dissolved in 1 ml of trifluoroacetic acid at -10° and stirred at this temperature. After 30 minutes, the reaction mixture was cooled to -78° and freeze-dried to give the yellow solid. Purification of the crude material by preparative tlc on silica gel (1% NH4OH in 5% MeOH/CH2Cl2) gave 28 mg of the title compound.

Workup

  1. customthe residue was purified on silica gel (5% MeOH/CH2Cl2)
  2. customto give the 65 mg of BOC protected compound
  3. stirringstirred at this temperature
  4. waitAfter 30 minutes
  5. temperaturethe reaction mixture was cooled to -78°
  6. customfreeze-dried
  7. customto give the yellow solid
  8. customPurification of the crude material by preparative tlc on silica gel (1% NH4OH in 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7e0b9f46689149f9a6f8f3561382c66f
Source dataset
uspto-grants-1993_05
Patent number
US05208228

Reaction notes

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