Hydrogen Bromide → HCID 22827679, compound

HRID 2418188Notes

Reaction equation

HRID 2418188 reaction equation
C([O:5][C:6](=[O:48])[C@H:7]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:8][C:9](=[O:40])[CH2:10][N:11]([C:21](=[O:39])[C@H:22]([CH3:38])[NH:23][C@H:24]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)(C)(C)C.[BrH:49].CCOCC>C(O)(=O)C>[BrH:49].[CH2:36]([O:35][C:33]([C@@H:24]([NH:23][C@H:22]([C:21]([N:11]([CH:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20]1)[CH2:10][C:9]([NH:8][C@H:7]([C:6]([OH:48])=[O:5])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:40])=[O:39])[CH3:38])[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:34])[CH3:37]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 13385099HCID 13385099, compound

Product 1

HCID 22827679HCID 22827679, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanyl-N-(2-indanyl)glycyl-L-phenylalanine tert-butyl ester (1.8 g) is dissolved in 2 ml of acetic acid, and 3 ml of 30% hydrogen bromide in acetic acid is added. The mixture is reacted at room temperature for 10 minutes. The reaction mixture is shaken with 300 ml of ether and allowed to stand. The ether is then decanted off and to the precipitate is added ethyl acetate, whereby 1.35 g of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-N-(2-indanyl)glycyl-L-phenylalanine hydrobromide is obtained as colorless prisms melting at 177°-181° C. (decomposition).

Workup

  1. customThe mixture is reacted at room temperature for 10 minutes
  2. customThe ether is then decanted off and to the precipitate
  3. additionis added ethyl acetate

Sources & evidence

ORD record
ord-6e0c3fcbb7e643f28e80edde490d1fce
Source dataset
uspto-grants-1984_09
Patent number
US04472383

Reaction notes

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