2,6-Dichlorobenzothiazole → HCID 68996427, compound

HRID 1909734Notes

Reaction equation

HRID 1909734 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:23]1[S:24][C:25]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:26]=2[N:27]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:23]2[S:24][C:25]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:26]=3[N:27]=2)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 771762,6-DichlorobenzothiazoleHCID 68999591(R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68996427HCID 68996427, compoundYield 75%

Procedure

Followed the same procedure as that of step 1 in Example 99 with the use of (R)-2-(4-hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester ((147 mg, 0.5 mmol) and 2,6-dichloro-benzothiazole (102 mg, 0.5 mmol) to yield the title product (172 mg, 75% yield); 1H NMR (400 MHz, DMSO-d6); δ 1.41 (s, 9H), 1.75-2.04 (m, 4H), 3.24-3.35 (m, 2H), 3.89-4.12 (m, 3H), 7.08 (d, J=9.2 Hz, 2H), 7.38 (d, J=9.2 Hz, 2H), 7.45 (dd, J1=8.8 Hz, J2=2.0 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 8.07 (d, J=2.0 Hz, 1H).

Sources & evidence

ORD record
ord-0211ca8e74bd4dceb91531d6c4730ec4
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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