Toluene → (R)-7-(2-(4-(2-(4-(Benzo[d]thiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzylamino)-1-hydroxyethyl)-4-hydroxybenzo[d]thiazol-2(3H)-one formate

HRID 471252Notes

Reaction equation

HRID 471252 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]([N:19]1[CH2:24][C:23]2([CH2:29][CH2:28][N:27]([CH2:30][CH2:31][O:32][C:33]3[CH:61]=[CH:60][C:36]([CH2:37][N:38]([CH2:46][C@H:47]([OH:59])[C:48]4[C:56]5[S:55][C:54](=[O:57])[NH:53][C:52]=5[C:51]([OH:58])=[CH:50][CH:49]=4)C(=O)OC(C)(C)C)=[CH:35][CH:34]=3)[CH2:26][CH2:25]2)[O:22][CH2:21][CH2:20]1)=[O:18].C1(C)C=CC=CC=1>C(Cl)Cl>[CH:3]([OH:5])=[O:4].[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]([N:19]1[CH2:24][C:23]2([CH2:29][CH2:28][N:27]([CH2:30][CH2:31][O:32][C:33]3[CH:61]=[CH:60][C:36]([CH2:37][NH:38][CH2:46][C@@H:47]([C:48]4[C:56]5[S:55][C:54](=[O:57])[NH:53][C:52]=5[C:51]([OH:58])=[CH:50][CH:49]=4)[OH:59])=[CH:35][CH:34]=3)[CH2:26][CH2:25]2)[O:22][CH2:21][CH2:20]1)=[O:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989166(R)-tert-Butyl 4-(2-(4-(benzo[d]thiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate

Product 1

HCID 67292606(R)-7-(2-(4-(2-(4-(Benzo[d]thiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzylamino)-1-hydroxyethyl)-4-hydroxybenzo[d]thiazol-2(3H)-one formate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.25 mL) was added to a solution of (R)-tert-butyl 4-(2-(4-(benzo[d]thiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate (example 106, step c) (0.33 g) in DCM (4 mL) and the resulting mixture stirred for 10 minutes. Toluene (20 mL) was added and the mixture was evaporated in vacuo. The residue was azeotroped with toluene (3×20 mL). Purification was by preparative HPLC (Phenomenex Gemini®, Gradient: 5-40% acetonitrile in 0.1% aqueous formic acid). The fractions containing product were combined and freeze-dried to give the titled compound as a white solid. Yield 0.096 g.

Workup

  1. customthe mixture was evaporated in vacuo
  2. customThe residue was azeotroped with toluene (3×20 mL)
  3. customPurification
  4. additionThe fractions containing product
  5. customfreeze-dried

Sources & evidence

ORD record
ord-185816e038e24496a298ebc6e94672a6
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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