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Toluene → (R)-4-Hydroxy-7-(1-hydroxy-2-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzylamino)ethyl)benzo[d]thiazol-2(3H)-one formate

HRID 1689487
Notes
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Reaction equation

HRID 1689487 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[OH:8][C@H:9]([C:50]1[C:58]2[S:57][C:56](=[O:59])[NH:55][C:54]=2[C:53]([OH:60])=[CH:52][CH:51]=1)[CH2:10][N:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]2[CH2:49][CH2:48][C:32]3([O:37][CH2:36][CH2:35][N:34]([C:38]([C:40]4[N:41]=[C:42]([CH:45]([CH3:47])[CH3:46])[S:43][CH:44]=4)=[O:39])[CH2:33]3)[CH2:31][CH2:30]2)=[CH:22][CH:21]=1)C(=O)OC(C)(C)C.C1(C)C=CC=CC=1>C(Cl)Cl>[CH:3]([OH:5])=[O:4].[OH:60][C:53]1[C:54]2[NH:55][C:56](=[O:59])[S:57][C:58]=2[C:50]([C@@H:9]([OH:8])[CH2:10][NH:11][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][C:32]4([O:37][CH2:36][CH2:35][N:34]([C:38]([C:40]5[N:41]=[C:42]([CH:45]([CH3:47])[CH3:46])[S:43][CH:44]=5)=[O:39])[CH2:33]4)[CH2:48][CH2:49]3)=[CH:24][CH:25]=2)=[CH:51][CH:52]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989138(R)-tert-Butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl)carbamate

Product 1

HCID 67292711(R)-4-Hydroxy-7-(1-hydroxy-2-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzylamino)ethyl)benzo[d]thiazol-2(3H)-one formate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.7 mL) was added to a solution of (R)-tert-butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl)carbamate (example 108, step d) (0.122 g) in DCM (1.5 mL). The resulting mixture was stirred at RT for 10 min. Toluene (15 mL) was added and the reaction mixture was evaporated in vacuo. The residue was azeotroped twice with MeCN. The viscous yellow residue was purified by 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 0.052 g.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe residue was azeotroped twice with MeCN
  3. customThe viscous yellow residue was purified by HPLC (Phenomenex Gemini®, Gradient: 5-40% acetonitrile in 0.1% aqueous formic acid)
  4. additionThe fractions containing product
  5. customfreeze dried

Sources & evidence

ORD record
ord-9156930d01b1453fbd7077e2b3534e07
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148373B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes