Formaldehyde → HCID 178491878, compound

HRID 1404386Notes

Reaction equation

HRID 1404386 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:49][CH2:50][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH3:52])[C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]([NH:18][C@H:19]([B:36]2[O:44][CH:43]3[C:38]([CH3:48])([CH:39]4[CH2:45][CH:41]([CH2:42]3)[C:40]4([CH3:47])[CH3:46])[O:37]2)[CH2:20][C:21]2[C:22]([O:34][CH3:35])=[C:23]([CH:31]=[CH:32][CH:33]=2)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.[CH2:68]=[O:69]>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]([CH2:49][CH2:50][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH3:52])[C@H:9]1[CH2:14][CH2:13][C@H:12]([CH:15]([CH2:68][OH:69])[C:16]([NH:18][C@H:19]([B:36]2[O:44][CH:43]3[C:38]([CH3:48])([CH:39]4[CH2:45][CH:41]([CH2:42]3)[C:40]4([CH3:47])[CH3:46])[O:37]2)[CH2:20][C:21]2[C:22]([O:34][CH3:35])=[C:23]([CH:31]=[CH:32][CH:33]=2)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 2724682Lithium diisopropylamideHCID 178491873HCID 178491873, compound

Product 1

HCID 178491878HCID 178491878, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To tert-butyl 3-((2R)-2-(2-(trans-4-(tert-butoxycarbonyl(2-(tert-butoxycarbonyl(methyl)amino)ethyl)amino)cyclohexyl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate (110 mg) in THF (5 mL) was added LDA (2 M in benzene, 160 μL) at −76° C. The reaction mixture was stirred at same temperature for 30 min before formaldehyde (20 mg) was added. The reaction mixture was allowed to warm up to RT and stirred for 4 hr. Brine was added and extracted with EtOAc. The organic phase was dried and concentrated to afford the crude product which was used to next step without further purification.

Workup

  1. additionwas added
  2. extractionextracted with EtOAc
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7642651ac12f4bf2a2126d7d42aa6c65
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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