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

HRID 64964
Notes
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Reaction equation

HRID 64964 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-c7688d9bdcb5466090708ad794c41ee2
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04611056

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes