Hexachloroethane → HCID 86686953, compound

HRID 1402089Notes

Reaction equation

HRID 1402089 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([C:22]([NH:24][NH:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=2)=O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([C:22]2[N:27]3[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]3=[N:25][N:24]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86686952HCID 86686952, compound

Product 1

HCID 86686953HCID 86686953, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (990 mg, 4.18 mmol) was added portionwise to a solution of Intermediate 4a (707 mg, 2.09 mmol), triphenylphosphine (1.103 g, 4.18 mmol) and triethylamine (1.2 mL, 8.36 mmol) in dry THF (30 mL) at RT. The mixture was stirred for 2 h. The resulting precipitate was filtered off and the filtrate evaporated. The residue was purified by SCX-2, eluting with MeOH followed by 2M NH3 in MeOH, to give a pale orange coloured solid. This was triturated (diethyl ether) to give the title compound as a buff-coloured solid (540 mg, 80%). LCMS (Method 1): Rt 2.79 min, m/z 321 and 221(-Boc) [MH+].

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customthe filtrate evaporated
  3. customThe residue was purified by SCX-2
  4. washeluting with MeOH
  5. customto give a pale
  6. customThis was triturated (diethyl ether)

Sources & evidence

ORD record
ord-8b45b695dfb84872b967ee5b743b6bb5
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

Loading…