1,2-Dichloroethane → HCID 58909299, compound

HRID 1991500Notes

Reaction equation

HRID 1991500 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=1)[C@H:3]([OH:17])[CH2:4][NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([I:16])[CH:14]=2)[O:9][CH2:8][CH2:7]1.CC[C:29](O)=[O:30].C(Cl)CCl.C1C=C[C:39]2N(O)N=N[C:40]=2[CH:41]=1.CN(C=[O:50])C.C(Cl)Cl>CCN(CC)CC>[F:25][C:23]1[CH:24]=[C:19]([CH:20]=[C:21]([F:26])[CH:22]=1)[CH2:18][C@H:2]([NH:1][C:29](=[O:30])[C:40]([OH:50])([CH3:39])[CH3:41])[C@H:3]([OH:17])[CH2:4][NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([I:16])[CH:14]=2)[O:9][CH2:8][CH2:7]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 1032Propionic AcidHCID 757711-HydroxybenzotriazoleHCID 22350042dichloromethane N,N-dimethylformamideHCID 58909298HCID 58909298, compound

Product 1

HCID 58909299HCID 58909299, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-{[(4S)-6-iodo-3,4-dihydro-2H-chromen-4-yl]amino}butan-2-ol (1 equiv) was combined with 2-methylacetic acid, (1.25 equiv), EDC (1.5 equiv) and HOBt (1.5 equiv) in DMF/DCM (1:1, 10 mL). The reaction mixture was treated with Et3N and stirred at ambient temperature for 6h. HPLC determined that the amine had been consumed by this time, and the reaction mixture was poured onto EtOAc and washed with 1M HCl, then the organics were dried over MgSO4 and concentrated to give an oil which was purified by reverse phase preparative HPLC. HRMS (ESI+) calcd for C23H27F2IN2O4 m/z 561.1063 (M+H)+. Found 561.1047.

Workup

  1. customhad been consumed by this time
  2. additionthe reaction mixture was poured onto EtOAc
  3. washwashed with 1M HCl
  4. dry with materialthe organics were dried over MgSO4
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-3e9fc961aa364034849ecc5d6e7f2677
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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