HCID 86612277, compound → HCID 58868875, compound

HRID 1441988Notes

Reaction equation

HRID 1441988 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C@H:7]1[N:25]([CH3:26])[C:24](=[O:27])[C@H:23]([CH2:28][CH2:29][CH2:30][NH:31]C(=O)OCC2C=CC=CC=2)[NH:22][C:21](=[O:42])[C@@H:20]([NH:43]C(OCC2C=CC=CC=2)=O)[CH2:19][C:18]2[CH:54]=[C:14]([CH:15]=[CH:16][C:17]=2[O:55]CC2C=CC=CC=2)[C:13]2=[CH:63][C:9](=[C:10]([F:64])[CH:11]=[CH:12]2)[CH2:8]1)=[O:6]>[Pd].C(O)(=O)C.O.C(O)C>[NH2:43][C@H:20]1[CH2:19][C:18]2[CH:54]=[C:14]([CH:15]=[CH:16][C:17]=2[OH:55])[C:13]2=[CH:63][C:9](=[C:10]([F:64])[CH:11]=[CH:12]2)[CH2:8][C@@H:7]([C:5]([NH:4][CH2:3][CH2:2][NH2:1])=[O:6])[N:25]([CH3:26])[C:24](=[O:27])[C@H:23]([CH2:28][CH2:29][CH2:30][NH2:31])[NH:22][C:21]1=[O:42]

Participants

4

Reactant 1

HCID 86612277HCID 86612277, compound

Product 1

HCID 58868875HCID 58868875, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86584229Acetic acid ethanol waterSolvent

Procedure

25 mg (0.029 mmol) of benzyl {3-[(8S,11S,14S)-8-{[(2-aminoethyl)amino]carbonyl}-17-(benzyloxy)-14-{[(benzyloxy)carbonyl]-amino}-5-fluoro-9-methyl-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-11-yl]pro-pyl}carbamate (Example 30O) are added into a mixture of 5 ml of acetic acid/water/ethanol (4:1:1) mixture. 10 mg of palladium on activated carbon (10%) are added, and the mixture is hydrogenated under atmospheric pressure at RT for 15 h. The reaction mixture is filtered through prewashed kieselguhr, washed with ethanol, and the filtrate is concentrated in vacuo on a rotary evaporator. The residue is mixed with 0.1N hydrochloric acid and concentrated in vacuo. The remaining solid is dried under high vacuum. The trihydrochloride is converted into the tri(hydrotrifluoroacetate) by preparative HPLC (Kromasil 100C18, mobile phase acetonitrile/0.2% aqueous trifluoroacetic acid 5:95→95:5).

Workup

  1. filtrationThe reaction mixture is filtered through prewashed kieselguhr
  2. washwashed with ethanol
  3. concentrationthe filtrate is concentrated in vacuo on a rotary evaporator
  4. additionThe residue is mixed with 0.1N hydrochloric acid
  5. concentrationconcentrated in vacuo
  6. customThe remaining solid is dried under high vacuum

Sources & evidence

ORD record
ord-f3dbf1777fd14854833c938d6b249848
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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