Boron tribromide → HCID 70556883, compound

HRID 408612Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:42])[CH2:5][N:6]([C:15]([C:17]1([CH2:33][O:34]CC2C=CC=CC=2)[CH2:20][CH2:19][N:18]1[C:21](=[O:32])[CH2:22][C:23]1[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[S:26][CH:27]=1)=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:42])[CH2:5][N:6]([C:15]([C:17]1([CH2:33][OH:34])[CH2:20][CH2:19][N:18]1[C:21](=[O:32])[CH2:22][C:23]1[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[S:26][CH:27]=1)=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [[1-(2-benzo[b]thiophen-3-yl-acetyl)-2-benzyloxymethyl-azetidine-2-carbonyl]-(4-chloro-benzyl)-amino]-acetic acid ethyl ester, Intermediate 163 (1 eq.) in DCM at 0° C. was added BBr3. The reaction was stirred at 0° C. for 2 h. The crude was diluted with DCM and poured into a saturated aqueous solution of NaHCO3. The layers were separated, the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with DCM/MeOH: 100/0 to 95/5) to afford [[1-(2-benzo[b]thiophen-3-yl-acetyl)-2-hydroxymethyl-azetidine-2-carbonyl]-(4-chloro-benzyl)-amino]-acetic acid ethyl ester.

Workup

customThe layers were separated
dry with materialthe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude was purified by chromatography on silica gel (elution with DCM/MeOH: 100/0 to 95/5)

Sources & evidence

ORD record: ord-9eb01d6c708242008a3508c585e5d582
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

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