1-Hydroxybenzotriazole → HCID 86757665, compound

HRID 2269364Notes

Reaction equation

HRID 2269364 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@@H:25]([N:29]([CH:37]=[O:38])[O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:26][CH2:27][CH3:28])[C:11]([O:13]C2C(F)=C(F)C(F)=C(F)C=2F)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:39]1[CH:43]=[N:42][N:41]=[C:40]1[NH:44][C:45](=[O:63])[C@@H:46]([NH2:62])[CH2:47][CH2:48][CH2:49][CH2:50][NH:51][C:52]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)=[O:53].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:55]([O:54][C:52]([NH:51][CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]([NH:62][C:11](=[O:13])[C@H:10]([CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@@H:25]([N:29]([CH:37]=[O:38])[O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)[CH2:26][CH2:27][CH3:28])[C:45](=[O:63])[NH:44][C:40]1[S:39][CH:43]=[N:42][N:41]=1)=[O:53])[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 70073493HCID 70073493, compoundHCID 86757664HCID 86757664, compound

Product 1

HCID 86757665HCID 86757665, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of pentafluorophenyl (2R,3S)-2-(3-phenyl-1-propyl)-3-(formyl-2-tetrahydropyranyloxyamino)hexanoate (90 mg, 0.166 mmol) in DMF (0.5 mL) is added (2S)-6-benzyloxycarbonylamino-2-aminohexanoic acid 1,3,4-thiadiazol-2-ylamide (78 mg, 0.215 mmol) and HOBt ( 2.2 mg, 0.017 mmol). The resulting solution is heated to 50° C. and is stirred for 18 h. The reaction mixture is cooled to 25° C., concentrated in vacuo, diluted with 20 mL of EtOAc, and washed with 1 M aqueous sodium carbonate solution. The organic layer is dried over magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (elution with 2:1 EtOAc-hexane) to provide (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(3-phenyl-1-propyl)hexanoic acid [(1S)-5-benzyloxycarbonylamino-1-(1,3,4-thiadiazol-2-ylcarbamoyl)-1-pentyl]amide as an oil (24.1 mg, 25% yield). APCI-MS m/z 745 (M+Na)+.

Workup

  1. temperatureThe reaction mixture is cooled to 25° C.
  2. concentrationconcentrated in vacuo
  3. additiondiluted with 20 mL of EtOAc
  4. washwashed with 1 M aqueous sodium carbonate solution
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (elution with 2:1 EtOAc-hexane)

Sources & evidence

ORD record
ord-418047d6c222402ea8cafa75da697d0c
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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