HCID 66927417, compound → HCID 86669322, compound

HRID 2170262Notes

Reaction equation

HRID 2170262 reaction equation
[C:1]([N:8]([CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])[C:9](=[O:19])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1([CH:32]([S:39]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)(=[O:41])=[O:40])[CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36])C=CC=CC=1>N1C=CC=CC=1.ClCCl.ClCCl>[C:1]([N:8]([CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][O:23][S:35]([CH2:34][CH2:33][CH2:32][S:39]([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=[O:41])=[O:40])(=[O:36])=[O:37])[C:9](=[O:19])[C@H:10]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH2:11])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

5

Reactant 2

HCID 66927417HCID 66927417, compoundHCID 86669323HCID 86669323, compound

Product 1

HCID 86669322HCID 86669322, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21875418Pyridine methylene chlorideSolvent

Procedure

To a stirred solution of 3-(N-Boc-L-phenylalaninamido)-2,2-dimethylpropanol from Step 1 (2 mmol) in a mixture of pyridine/dichloromethane (5 mL:10 mL) was added a solution of phenyl 3-phenoxysulfonyl-1-propanesulfonyl chloride (Example 1 (b)) (2.2 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 15 h, then concentrated and rediluted with ethyl acetate and aqueous hydrochloric acid (1 N). The organic phase was isolated, washed with aqueous hydrochloric acid (1 N) and concentrated. The residual material was purified by silica gel chromatography using hexanes/ethyl acetate (70:30 to 50:50) as eluent to afford 3-phenoxysulfonyl-1-propanesulfonic acid 3-(N-Boc-L-phenylalaninamido)-2,2-dimethylpropyl ester.

Workup

  1. concentrationconcentrated
  2. additionrediluted with ethyl acetate and aqueous hydrochloric acid (1 N)
  3. customThe organic phase was isolated
  4. washwashed with aqueous hydrochloric acid (1 N)
  5. concentrationconcentrated
  6. customThe residual material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e3c947fe828e45c8b0dfe64f60a123ce
Source dataset
uspto-grants-2015_06
Patent number
US09051248B2

Reaction notes

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