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Dicyclohexylcarbodiimide → 5-tert-butyloxycarbonylamino acetoxy-12H-benzo[a]phenothiazine

HRID 2352218
Notes
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Reaction equation

HRID 2352218 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[CH:30]=[C:29]2[C:20]([NH:21][C:22]3[C:27]([S:28]2)=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:19]2[CH:31]=[CH:32][CH:33]=[CH:34][C:18]=12.[C:35]([O:39][C:40]([NH:42][CH2:43][C:44](O)=[O:45])=[O:41])([CH3:38])([CH3:37])[CH3:36]>C1COCC1.CN(C1C=CN=CC=1)C>[C:35]([O:39][C:40]([NH:42][CH2:43][C:44]([O:16][C:17]1[CH:30]=[C:29]2[C:20]([NH:21][C:22]3[C:27]([S:28]2)=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:19]2[CH:31]=[CH:32][CH:33]=[CH:34][C:18]=12)=[O:45])=[O:41])([CH3:38])([CH3:37])[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 137124785-hydroxy-12H-benzo[a]phenothiazine

Product 1

HCID 137124875-tert-butyloxycarbonylamino acetoxy-12H-benzo[a]phenothiazine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

Dicyclohexylcarbodiimide (21 g) was added to a solution of 5-hydroxy-12H-benzo[a]phenothiazine (4.2 g) and N-tert-butyloxycarbonyl glycine (8.4 g) in THF (150 ml) followed by the addition of DMAP (0.2 g). The reaction mixture was stirred for 15 minutes, filtered and the filtrate evaporated to dryness. The residue was dissolved in EtOAc, washed with a solution of NaHCO3, dried and evaporated to dryness. The resulting oily residue was chromatographed on silica gel (5% EtOAc/CH2Cl2) to afford 5-tert-butyloxycarbonylamino acetoxy-12H-benzo[a]phenothiazine. m.p. 175° as an intermediate.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with a solution of NaHCO3
  5. customdried
  6. customevaporated to dryness
  7. customThe resulting oily residue was chromatographed on silica gel (5% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-5cff60d863fd4b23b1ff57b0a9bba5d6
Source dataset
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04876246

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes