Hydrochloric Acid → HCID 67074072, compound

HRID 2095587Notes

Reaction equation

HRID 2095587 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[N:10]([CH2:11][CH2:12][CH2:13][C:14](OC(C)(C)C)=[O:15])[C:9](=[O:21])[CH:8]([CH3:22])[N:7]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:6]1)=[O:4].Cl.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:59]1[C:61]2([CH2:66][CH2:65][NH:64][CH2:63][C@H:62]2[OH:67])[CH2:60]1.C(N(CC)CC)C>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]([C@H:5]1[N:10]([CH2:11][CH2:12][CH2:13][C:14]([N:64]2[CH2:65][CH2:66][C:61]3([CH2:59][CH2:60]3)[C@H:62]([OH:67])[CH2:63]2)=[O:15])[C:9](=[O:21])[CH:8]([CH3:22])[N:7]([C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[CH2:6]1)=[O:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride2×HCID 67074149HCID 67074149, compound

Product 1

HCID 67074072HCID 67074072, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.15 g (0.3 mmol) of (S)-4-(3-tert-butoxycarbonyl-propyl)-6-methyl-5-oxo-piperazine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester in 5 ml of THF was added 1.5 ml of 37% hydrochloric acid. The reaction was stirred for 2 h after which time it was evaporated to dryness. The residue was redissolved in 2 m of DMF, 0.14 g (0.4 mmol) of HATU and 0.06 g (0.4 mmol) of (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (intermediate 2) were added followed by 0.2 ml (1.2 mmol) of triethylamine. The reaction was stirred for 1 h after which time the solvent was evaporated, the residue redissolved in EtOAc, washed with water, brine, dried (Na2SO4) and concentrated to give after flash silica gel column (CH2Cl2/MeOH 95:5) the title compound in quantitative yield as a colorless foam. MS: 502.4 (MH+).

Workup

  1. customwas evaporated to dryness
  2. additionwere added
  3. stirringThe reaction was stirred for 1 h after which time the solvent
  4. customwas evaporated
  5. dissolutionthe residue redissolved in EtOAc
  6. washwashed with water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5a34847871674af296f804267179eb0e
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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