Water → HCID 67320554, compound

HRID 2274555Notes

Reaction equation

HRID 2274555 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:21][C:22]([NH:24][C@@H:25]1[CH2:39][C:38]2=[CH:40][CH:41]=[C:35]([CH:36]=[CH:37]2)[NH:34][C:33](=[O:42])[CH2:32][CH2:31][O:30][CH2:29][C@H:28]([CH:43]([CH3:45])[CH3:44])[NH:27][C:26]1=[O:46])=[O:23])[C:14]([O:16]C(C)(C)C)=[O:15])=O)(C)(C)C.O.C([SiH](C(C)C)C(C)C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:21][C:22]([NH:24][C@@H:25]1[CH2:39][C:38]2=[CH:37][CH:36]=[C:35]([CH:41]=[CH:40]2)[NH:34][C:33](=[O:42])[CH2:32][CH2:31][O:30][CH2:29][C@H:28]([CH:43]([CH3:44])[CH3:45])[NH:27][C:26]1=[O:46])=[O:23])[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 138754Silane, tris(1-methylethyl)-HCID 67028557HCID 67028557, compound

Product 1

HCID 67320554HCID 67320554, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

20.0 mg (0.03 mmol) of tert-butyl (S)-6-tert-butoxycarbonylamino-2-[3((8S,11R)-8-isopropyl-3,10-dioxo-6-oxa-2,9-diazabicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-yl)ureido]hexanoate were stirred in a mixture of 0.95 ml of TFA, 25 μl of water and 25 μl of triisopropylsilane at room temp. for 2 h. After the reaction was complete, the mixture was concentrated in vacuo and codistilled with toluene several times. The crude product obtained in this way was purified by preparative HPLC (acetonitrile/water+addition of 0.1% TFA). 5 mg of the title compound were obtained in this way as trifluoroacetate in the form of a colorless amorphous material.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe crude product obtained in this way
  3. customwas purified by preparative HPLC (acetonitrile/water+addition of 0.1% TFA)

Sources & evidence

ORD record
ord-e2b5f4a83cac4ea1a8669c9e4680f210
Source dataset
uspto-grants-2015_09
Patent number
US09126955B2

Reaction notes

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