Diisopropylethylamine → (S)-N-(1-benzyloxycarbonyl-5-benzyloxycarbonyl-amino-pent-1-yl)-N-[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine

HRID 1609215Notes

Reaction equation

HRID 1609215 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[C@@H:10]([NH2:26])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15]C(OCC1C=CC=CC=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH:34]([CH3:36])[CH3:35])CC)(C)C.Br[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]2[N:55]([C:56]([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[N:54]=[N:53][N:52]=2)=[CH:41][CH:40]=1>CN(C)C=O>[CH2:1]([O:8][C:9]([C@@H:14]([NH:15][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]2[N:55]([C:56]([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[N:54]=[N:53][N:52]=2)=[CH:41][CH:40]=1)[CH2:13][CH2:12][CH2:11][CH:10]([NH2:26])[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:27])=[O:27])[C:35]1[CH:34]=[CH:36][CH:7]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7269426benzyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

Product 1

HCID 66577461(S)-N-(1-benzyloxycarbonyl-5-benzyloxycarbonyl-amino-pent-1-yl)-N-[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 g of (S)-2-amino-6-benzyloxycarbonylamino-hexanoic acid benzyl ester are dissolved in 250 ml of N,N-dimethylformamide. The solution is treated with 4.33 ml of N,N-diisopropyl-N-ethyl-amine, and the mixture is warmed to 80°, stirred for 30 minutes, treated with 4.44 g of 4-bromomethyl-2'-(1-triphenylmethyl-1H-tetrazol-5-yl)-biphenyl, stirred for 16 hours at 80° and then evaporated. The residue is worked up using water and ethyl acetate. The organic phase is dried and purified by means of flash-chromatography (200 g of silica gel; system N4). The (S)-N-(1-benzyloxycarbonyl-5-benzyloxycarbonyl-amino-pent-1-yl)-N-[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine is obtained in the form of a brown oil [Rf : 0.18 (system N3)].

Workup

  1. temperaturethe mixture is warmed to 80°
  2. stirringstirred for 16 hours at 80°
  3. customevaporated
  4. customThe organic phase is dried
  5. custompurified by means of flash-chromatography (200 g of silica gel; system N4)

Sources & evidence

ORD record
ord-71c5ba1054e24bf7a09ea2fcfadd7198
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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