Triethylamine → HCID 69960675, compound

HRID 427262Notes

Reaction equation

HRID 427262 reaction equation
[S:1]([O:5][C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8])([OH:4])(=[O:3])=O.[NH2:13][C:14]1[C:37]([Br:38])=[CH:36][C:17]([CH2:18][C@H:19]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([CH:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)[CH2:25][CH2:24]2)=[O:22])[NH2:20])=[CH:16][C:15]=1[Br:39].C(N(CC)CC)C>CN(C)C=O.C[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3C4C(=CC5OCOC=5C=4)[C@@H](C4C=C(OC)C(O)=C(OC)C=4)[C@@H]4[C@@H]3COC4=O)O[C@@H]2CO1.C1COP(NCCCl)(=O)N(CCCl)C1.[NH2-].[NH2-].Cl[Pt+2]Cl>[NH2:13][C:14]1[C:15]([Br:39])=[CH:16][C:17]([CH2:18][C@H:19]([C:21]([N:23]2[CH2:24][CH2:25][N:26]([CH:29]3[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]3)[CH2:27][CH2:28]2)=[O:22])[NH:20][S:1]([O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[OH:8])(=[O:3])=[O:4])=[CH:36][C:37]=1[Br:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 30838792-Hydroxyphenyl hydrogen sulfateHCID 53947371HCID 53947371, compound

Product 1

HCID 69960675HCID 69960675, compound

Reagents, catalysts & solvents 2

HCID 56841950ICE protocol 1CatalystHCID 6228DimethylformamideSolvent

Procedure

Whilst cooling externally with ice 1.377 g (7.998 mmol) of pyrocatechol sulfate was added to a solution of 2.000 g (3.974 mmol) of 1-(4-amino-3,5-dibromo-D-phenylalanyl)-4-(1-methyl-4-piperidinyl)piperazine and 0.61 mL (0.004 mmol) of triethylamine in 50 mL of dimethylformamide and the mixture was then stirred for 1 hour whilst still being cooled with ice and for 2 hours at room temperature. The reaction mixture was concentrated by evaporation in vacuo at a maximum bath temperature of +40° C., the residue was triturated with diethylether, dried in air and used in the next step without further purification. Yield: 2.68 g (100% of theory).

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation in vacuo at a maximum bath temperature of +40° C.
  2. customthe residue was triturated with diethylether
  3. customdried in air
  4. customused in the next step without further purification

Sources & evidence

ORD record
ord-1395aafb478a416db0c70ad3b21833be
Source dataset
uspto-grants-2001_11
Patent number
US06313097B1

Reaction notes

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