Diisopropylethylamine → HCID 480330, compound

HRID 429966Notes

Reaction equation

HRID 429966 reaction equation
[O:1]1[CH2:6][CH:5]([O:7][C:8](=[O:30])[NH:9][C@@H:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:11]([OH:22])[CH2:12][NH:13][CH2:14][C:15]([CH3:21])([CH3:20])[CH2:16][CH2:17][C:18]#[N:19])[CH2:4][O:3][CH2:2]1.[CH2:31]([O:38][C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N(CC)(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[O:1]1[CH2:6][CH:5]([O:7][C:8](=[O:30])[NH:9][C@@H:10]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@H:11]([OH:22])[CH2:12][N:13]([CH2:14][C:15]([CH3:21])([CH3:20])[CH2:16][CH2:17][C:18]#[N:19])[S:45]([C:42]2[CH:41]=[CH:40][C:39]([O:38][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:44][CH:43]=2)(=[O:47])=[O:46])[CH2:4][O:3][CH2:2]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 21356686HCID 21356686, compound

Product 1

HCID 480330HCID 480330, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

{(1S,2R)-1-Benzyl-3-(4-cyano-2,2-dimethyl-butylamino)-2-hydroxy-propyl}-carbamic acid [1,3]dioxan-5-yl ester (14.8 mg, 0.04 mmol) was combined with 4-benzyloxybenzenesulfonyl chloride (12.0 mg, 1.2 eq.) in anhydrous DMF (1 mL). Solution was chilled to 0° C. and N(i-Pr)2Et (18.4 μL, 3 eq.) was added. Reaction was allowed to warm to room temperature and stirred for 5 hours. Reaction mixture was diluted in EtOAc (10 mL) and washed with sat. NaHCO3 (10 mL), 0.5 N KHSO4 (10 mL) and brine (10 mL). Organic phase was dried with MgSO4 and solvent was removed in vacuo. Purification by preparative TLC (1:1, EtOAc:Hex). Recovered 4.2 mg (18%) of the product as a colorless residue. MS (ES); 666.2 (M+1), HPLC; tR=13.24 min. (98%).

Workup

  1. customReaction
  2. temperatureto warm to room temperature
  3. customReaction mixture
  4. washwashed with sat. NaHCO3 (10 mL), 0.5 N KHSO4 (10 mL) and brine (10 mL)
  5. dry with materialOrganic phase was dried with MgSO4 and solvent
  6. customwas removed in vacuo
  7. customPurification by preparative TLC (1:1, EtOAc:Hex)
  8. customRecovered 4.2 mg (18%) of the product as a colorless residue

Sources & evidence

ORD record
ord-d8fb3d66acf54d2ca4199e89003191e1
Source dataset
uspto-grants-2001_11
Patent number
US06319946B1

Reaction notes

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