Boron tribromide → HCID 57777394, compound

HRID 660563Notes

Reaction equation

HRID 660563 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][C:27]=1[N:28]1[CH2:32][C:31](=[O:33])[NH:30][S:29]1(=[O:35])=[O:34])[CH2:12][C@@H:13]1[NH:19][C:18](=[O:20])[C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[CH:15]=[CH:14]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][C:27]=1[N:28]1[CH2:32][C:31](=[O:33])[NH:30][S:29]1(=[O:35])=[O:34])[CH2:12][C@@H:13]1[NH:19][C:18](=[O:20])[C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[CH:15]=[CH:14]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68839778HCID 68839778, compound

Product 1

HCID 57777394HCID 57777394, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of (S)-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-2,3-dihydrobenzo[c]azepin-1-one in methylene chloride (2 mL) at −10° C. is added 0.3 mL of BBr3. The mixture is stirred at −10° C. for 30 min and is quenched with water. The aqueous phase is separated and lyophilized to give the title compound: 1H NMR (DMSO-d6) δ 9.61 (br s, 1H), 8.30 (d, J=5.56 Hz, 1H), 7.84 (d, J=7.58 Hz, 1H), 7.52 (t, J=7.07 Hz, 1H), 7.40 (t, J=7.58 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.24 (d, J=8.08 Hz, 1H), 6.71 (m, 3H), 6.17 (m, 1H), 4.30 (s, 2H), 3.64 (m, 1H), 2.68 (m, 1H), 2.77 (m, 1H).

Workup

  1. customis quenched with water
  2. customThe aqueous phase is separated

Sources & evidence

ORD record
ord-dde1b0e14f12480ba21795e1ba4a84ea
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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